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

HRID 409899Notes

Reaction equation

HRID 409899 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 10e (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 10f (light pink powder).

Workup

  1. concentrationThe reaction mixture was then concentrated

Sources & evidence

ORD record
ord-e38ea0e05c464da6a9cb43d1cccd9342
Source dataset
uspto-grants-2014_06
Patent number
US08759533B2

Reaction notes

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