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

HRID 267862Notes

Reaction equation

HRID 267862 reaction equation
[Br:1]Br.[C:3]1([C:9]2[C:10]3[CH:21]=[CH:20][CH:19]=[CH:18][C:11]=3[S:12][C:13]=2[C:14]([O:16][CH3:17])=[O:15])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.S(=O)(O)[O-].[Na+]>C(O)(=O)C>[Br:1][C:20]1[CH:19]=[CH:18][C:11]2[S:12][C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:9]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:10]=2[CH:21]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 227635043-Phenylbenzo[b]thiophene-2-carboxylic acid methyl esterHCID 23665763Sodium Bisulfite

Product 1

HCID 22763497Methyl 5-bromo-3-phenylbenzo[b]thiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Add 29.3 g. bromine (10 ml; 0.37 mole) to 8.0 g. (0.03 mole) of methyl 3-phenylbenzo [b]thiophene-2-carboxylate in 100 ml. of acetic acid and stir the mixture overnight at room temperature. Add a saturated solution of sodium bisulfite. Decant the supernatant and wash the oil with water. Triturate with methanol. Recrystallize from methanol to yield the title compound; m.p. 125°-126°.

Workup

  1. additionAdd 29.3 g
  2. customDecant the supernatant
  3. washwash the oil with water
  4. customTriturate with methanol
  5. customRecrystallize from methanol

Sources & evidence

ORD record
ord-571d02105dea49e69a3eb6debf900480
Source dataset
uspto-grants-1976_03
Patent number
US03944672

Reaction notes

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