Water → 2-Bromo-1-(5-phenyl-2-thienyl)-1-ethanone

HRID 2398084Notes

Reaction equation

HRID 2398084 reaction equation
[C:1]([C:4]1[S:5][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:7][CH:8]=1)(=[O:3])[CH3:2].[Br:15]Br.O>C(O)(=O)C>[C:9]1([C:6]2[S:5][C:4]([C:1]([CH2:2][Br:15])=[O:3])=[CH:8][CH:7]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 49624811-(5-phenylthiophen-2-yl)ethanone

Product 1

HCID 27763102-Bromo-1-(5-phenyl-2-thienyl)-1-ethanone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-acetyl-5-phenylthiophene (11.7 g, 0.058 mole), described in Examples 1 and 2, in 100 ml of glacial acetic acid is treated dropwise with bromine (9.3 g, 0.058 mole). The mixture is stirred for 1/2 hr, poured into cold water and extracted with chloroform. The extract is washed with water, 5% NaHCO3 and brine, dried (H2CO3) and concentrated to give a yellow solid. The solid is subjected to chromatography on silica gel to give bromomethyl 5-phenyl-2-thienyl ketone (ArCOCHR2Y; Ar is 5-phenyl-2-thienyl, R2 = H and Y = Br) mp 114° C.

Workup

  1. extractionextracted with chloroform
  2. washThe extract is washed with water, 5% NaHCO3 and brine
  3. customdried (H2CO3)
  4. concentrationconcentrated
  5. customto give a yellow solid

Sources & evidence

ORD record
ord-5f972e512ef343c4b4c155b4bf246738
Source dataset
uspto-grants-1977_05
Patent number
US04024156

Reaction notes

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