Water → 5-Bromothiophene-3-carboxylic acid

HRID 1888411Notes

Reaction equation

HRID 1888411 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=[O:7])=[CH:2]1.[Br:9]Br.O>C(O)(=O)C>[Br:9][C:5]1[S:1][CH:2]=[C:3]([C:6]([OH:8])=[O:7])[CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6918Thiophene-3-carboxylic acidHCID 24408Bromine

Product 1

HCID 120399785-Bromothiophene-3-carboxylic acidYield 26%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of thiophene-3-carboxylic acid (5.00 g, 39.0 mmol) in acetic acid (140 mL), was added dropwise, a solution of bromine (6.60 g, 40.0 mmol) in acetic acid (40 mL). The reaction mixture was stirred for 30 minutes and then poured into water. The resultant solid was collected by filtration to afford the title compound as a grey solid (2.07 g, 26%). LCMS (Method B): RT=2.9 min, M+H+=208.

Workup

  1. filtrationThe resultant solid was collected by filtration

Sources & evidence

ORD record
ord-59e3bec80e3c4d90a69f2b1f611cddf8
Source dataset
uspto-grants-2013_08
Patent number
US08501765B2

Reaction notes

Loading…