Bromine → Methyl 3-bromo-2-methylbenzo[b]thiophene-5-carboxylate

HRID 280596Notes

Reaction equation

HRID 280596 reaction equation
[Br:1]Br.[CH3:3][O:4][C:5]([C:7]1[CH:16]=[CH:15][C:10]2[S:11][C:12]([CH3:14])=[CH:13][C:9]=2[CH:8]=1)=[O:6].C([O-])(=O)C.[Na+]>C(Cl)(Cl)Cl>[CH3:3][O:4][C:5]([C:7]1[CH:16]=[CH:15][C:10]2[S:11][C:12]([CH3:14])=[C:13]([Br:1])[C:9]=2[CH:8]=1)=[O:6]

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 136630372-Methylbenzo[b]thiophene-5-carboxylic acid methyl ester

Product 1

HCID 13663045Methyl 3-bromo-2-methylbenzo[b]thiophene-5-carboxylateYield 60.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Bromine (2.08 g) was added dropwise to a stirred mixture of 2-methylbenzo[b]thiophene-5-carboxylic acid methyl ester (2.40 g) and anhydrous sodium acetate (2.40 g) in chloroform (50 ml). The mixture was stirred for 2 hours at room temperature and then washed with water, sodium bicarbonate solution and dried (NaSO4). Evaporation of the chloroform gave a solid which was crystallised from methanol/water to give 3-bromo-2-methylbenzo[b]thiophene-5-carboxylic acid methyl ester (2.00 g), m.p. 84°-85°.

Workup

  1. washwashed with water, sodium bicarbonate solution
  2. dry with materialdried (NaSO4)
  3. customEvaporation of the chloroform
  4. customgave a solid which
  5. customwas crystallised from methanol/water

Sources & evidence

ORD record
ord-750dac6955404ad098cee0f9879ff20e
Source dataset
uspto-grants-1986_05
Patent number
US04590200

Reaction notes

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