Water → 2-Bromo-5-benzoylthiophene

HRID 894258Notes

Reaction equation

HRID 894258 reaction equation
[Br:1][C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.[C:7](Cl)(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(Cl)Cl.O>CCOCC>[C:7]([C:4]1[S:3][C:2]([Br:1])=[CH:6][CH:5]=1)(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 7412Benzoyl chlorideHCID 138512-Bromothiophene

Product 1

HCID 2986042-Bromo-5-benzoylthiophene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2-Bromothiophene (9.7 ml., 0.1 mole), benzoyl chloride (11.6 ml., 0.1 mole) and stannic chloride (11.5 ml., 0.1 mole) were combined in 100 ml. of methylene chloride and stirred at room temperature for 4 hours. The reaction mixture was cooled to room temperature, water (65 ml.) was added and the two phase system stirred for 20 minutes. Ether (165 ml.) was added, the organic phase was separated, back-washed with 20 ml. of 1 N sodium hydroxide and twice with 20 ml. of water, and concentrated to an oil (20.8 g.) which crystallized on standing. The crude was melted by warming with 25 ml. of hexane (two phases formed) and cooled to yield purified crystalline 5-benzoyl-2-bromothiophene (16.5 g., m/e 266/268).

Workup

  1. customthe organic phase was separated
  2. washback-washed with 20 ml
  3. concentrationof water, and concentrated to an oil (20.8 g.) which
  4. customcrystallized
  5. temperatureby warming with 25 ml
  6. temperatureof hexane (two phases formed) and cooled
  7. customto yield
  8. custompurified crystalline 5-benzoyl-2-bromothiophene (16.5 g., m/e 266/268)

Sources & evidence

ORD record
ord-9dc5dab418aa413ab28c56dce0b67ce6
Source dataset
uspto-grants-1981_08
Patent number
US04282246

Reaction notes

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