Bromine → 2-Bromo-1-(5-bromothiophen-2-yl)ethan-1-one

HRID 507656Notes

Reaction equation

HRID 507656 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7](=[O:9])[CH3:8])=[CH:4][CH:3]=1.[Br:10]Br>C(O)(=O)C>[Br:10][CH2:8][C:7]([C:5]1[S:6][C:2]([Br:1])=[CH:3][CH:4]=1)=[O:9]

Participants

4

Reactant 2

HCID 24408BromineHCID 793352-Acetyl-5-bromothiophene

Product 1

HCID 19883982-Bromo-1-(5-bromothiophen-2-yl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

1-(5-Bromothiophen-2-yl)ethanone (1 g, 4.87 mmol) was dissolved in glacial acetic acid (5 mL) and treated with bromine (0.25 mL) in acetic acid (2 mL) added dropwise. The reaction was stirred at ambient temperature overnight. The volatiles were removed in vacuo while care was taken so as to keep the bath temperature under 40° C. The residue was dissolved in dichloromethane, washed with saturated aqueous sodium bicarbonate, water and brine. The organic layer was then dried with sodium sulfate, concentrated and purified by flash chromatography using a gradient of 10 to 30% of ethyl acetate in hexanes to yield a off-white solid (0.85 g).

Workup

  1. additionadded dropwise
  2. customThe volatiles were removed in vacuo while care
  3. customunder 40° C
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washwashed with saturated aqueous sodium bicarbonate, water and brine
  6. dry with materialThe organic layer was then dried with sodium sulfate
  7. concentrationconcentrated
  8. custompurified by flash chromatography

Sources & evidence

ORD record
ord-e9d0c691d59747ad82a759c125d86fe2
Source dataset
uspto-grants-2010_08
Patent number
US07786132B2

Reaction notes

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