Acetic Acid → 3-Bromobenzo[B]thiophene-7-carboxamide

HRID 605955Notes

Reaction equation

HRID 605955 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[CH:7][CH:8]=[C:9]([C:10]([NH2:12])=[O:11])[C:2]1=2.C(O)(=O)C.C1C(=O)N([Br:24])C(=O)C1>ClCCl>[Br:24][C:4]1[C:3]2[CH:6]=[CH:7][CH:8]=[C:9]([C:10]([NH2:12])=[O:11])[C:2]=2[S:1][CH:5]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 67184N-bromobutanimideHCID 19602336Benzo[B]thiophene-7-carboxamide

Product 1

HCID 575900333-Bromobenzo[B]thiophene-7-carboxamideYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of benzo[b]thiophene-7-carboxylic acid amide (500 mg, 2.82 mmol) in dichloromethane (5 mL) is stirred at rt and acetic acid (5 mL) is added followed by NBS (750 mg, 4.23 mmol, 1.5 equiv.). The reaction is stirred at room temperature for 1 hour at which point LC-MS analysis shows full conversion of the starting material to the desired compound (79%) and dibrominated material (21%). The reaction is diluted with water (50 mL), neutralized with aqueous potassium disulfite, followed by sodium bicarbonate. The aqueous layer is then extracted with dichloromethane and the resulting organic layers are combined, washed with brine, dried over Na2SO4 and evaporated. The crude material is purified by LC using DCM as the eluent to afford the title compound as a white solid (300 mg, 41%).

Sources & evidence

ORD record
ord-c263e29514fe426aa1d2750b9f0f8c68
Source dataset
uspto-grants-2011_03
Patent number
US07915256B2

Reaction notes

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