Dimethylformamide → 3-Fluoro-5-phenyl-benzo[b]thiophene-2-carbonyl chloride

HRID 468155Notes

Reaction equation

HRID 468155 reaction equation
[F:1][C:2]1[C:3]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:11]=[CH:10][C:4]=2[S:5][C:6]=1[C:7](O)=[O:8].C(Cl)(C([Cl:24])=O)=O.CN(C=O)C>C(Cl)Cl>[F:1][C:2]1[C:3]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:11]=[CH:10][C:4]=2[S:5][C:6]=1[C:7]([Cl:24])=[O:8]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 596258253-Fluoro-5-phenyl-benzo[b]thiophene-2-carboxylic acid

Product 1

HCID 596257253-Fluoro-5-phenyl-benzo[b]thiophene-2-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 52d (136.2 mg, 0.5 mmol) in CH2Cl2 (5 mL) at room temperature was added (COCl)2 (0.064 mL, 0.75 mmol), followed by DMF (0.01 mL, 0.125 mmol). The reaction mixture was stirred at room temperature for 18 h. The reaction mixture was then concentrated to give compound 52e (light pink powder), which was used in the next reaction without further purification.

Workup

  1. concentrationThe reaction mixture was then concentrated

Sources & evidence

ORD record
ord-fc4e7ecd65ba4777aea6cf8ecb3eab53
Source dataset
uspto-grants-2014_01
Patent number
US08623858B2

Reaction notes

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