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

HRID 403296Notes

Reaction equation

HRID 403296 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 13d (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 13e as a 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-a0994920e26b416889a4bff7ba927092
Source dataset
uspto-grants-2014_06
Patent number
US08748417B2

Reaction notes

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