IP Library Granted Patent US 11,236,062
Granted Patent B2
US 11,236,062 · App. 16/089,633 · Granted Feb 1, 2022

Method for producing 5-(bromomethyl)-1-benzothiophene

Inventors: Kentaro Ishihara (Toyama, JP); Tsuyoshi Arai (Kaisei, JP)
Assignees: FUJIFILM Toyama Chemical Co., Ltd.; FUJIFILM CORPORATION
C07D333/54B01J19/123B01J19/127B01J2219/0877B01J2219/1203
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Quick Facts
Patent No.
US 11,236,062
App. No.
16/089,633
Granted
Feb 1, 2022
Kind
B2
Abstract

Provided is a method for industrially producing 5-(bromomethyl)-1-benzothiophene. The production method according to the present invention comprises: (1) a step for introducing 5-methyl-1-benzothiophene, a brominating agent, and a solvent into a reactor; (2) a step for emitting light having a wavelength range of 200-780 nm inside the reactor; and (3) a step for recovering 5-(bromomethyl)-1-benzothiophene from the reactor.

Claims (14)

1. A method for producing 5-bromomethyl-1-benzothiophene, comprising:

(1) introducing 5-methyl-1-benzothiophene, a brominating agent and a solvent into a reactor to obtain a reaction mixture;

(2) irradiating the interior of the reactor with light having a wavelength range of 200 to 780 nm; and

(3) recovering the reaction mixture comprising 5-bromomethyl-1-benzothiophene from the reactor, wherein the 5-bromomethyl-1-benzothiophene is directly used without isolation in a next cyanation step,

wherein

the reactor is a flow-type photochemical reactor,

the solvent is at least one selected from the group consisting of methyl acetate and ethyl acetate,

a peak area ratio of 5-bromomethyl-1-benzothiophene in the reaction mixture is 79% or more,

a peak area ratio of 5-dibromomethyl-1-benzothiophene in the reaction mixture is 3% or less, and

a peak area ratio of 3-bromo-5-methyl-1-benzothiophene in the reaction mixture is 3% or less.

2. The method according to claim 1 , wherein the brominating agent is at least one selected from the group consisting of bromine, N-bromocaprolactam, N-bromosuccinimide, 1,3-dibromo-5,5-dimethylhydantoin, a bromine-pyridine complex and copper(II) bromide.

3. The method according to claim 1 , wherein the brominating agent is at least one selected from the group consisting of N-bromosuccinimide and 1,3-dibromo-5,5-dimethylhydantoin.

4. The method according to claim 1 , wherein the brominating agent is 1,3-dibromo-5,5-dimethylhydantoin.

5. The method according to claim 1 , wherein a reaction temperature is from 5 to 70° C.

Assignments (2)
MERGER AND CHANGE OF NAME Recorded Nov 19, 2018
From: FUJIFILM RI PHARMA CO., LTD.; TOYAMA CHEMICAL CO., LTD.
To: FUJIFILM TOYAMA CHEMICAL CO., LTD.
Reel/Frame 047536/0252 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 17, 2018
From: ISHIHARA, KENTARO; ARAI, TSUYOSHI
To: TOYAMA CHEMICAL CO., LTD.; FUJIFILM CORPORATION
Reel/Frame 047198/0829 →
Priority Claims (1)
JP JP2016-071574 · Mar 31, 2016 · national
Continuity (1)
Related Publication 20190119242A1 · Apr 25, 2019