Dimethylformamide → 2-n-Butyl-3-(3'-bromo-4'-hydroxybenzoyl)-benzofuran

HRID 1283635Notes

Reaction equation

HRID 1283635 reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[CH:22]=[CH:21][CH:20]=[CH:19][C:8]=2[C:9]=1[C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)[CH2:2][CH2:3][CH3:4].[Br:23]N1C(=O)CCC1=O.CN(C)C=O>O>[CH2:1]([C:5]1[O:6][C:7]2[CH:22]=[CH:21][CH:20]=[CH:19][C:8]=2[C:9]=1[C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([Br:23])[CH:12]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 96670(2-Butylbenzofuran-3-yl) (4-hydroxyphenyl) ketone

Product 1

HCID 215186382-n-Butyl-3-(3'-bromo-4'-hydroxybenzoyl)-benzofuran

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 10.0 g. (0.034 mol.) of 2-n-butyl-3-(4'-hydroxybenzoyl)benzofuran and 6.1 g. (0.034 mol.) of N-bromosuccinimide in 150 ml. of damp dimethylformamide was refluxed for 12 hours. The reaction mixture was poured into water and extracted with chloroform. The extracts were washed repeatedly with water, then dried (Na2SO4) and concentrated to give 2-n-butyl-3-(3'-bromo-4'-hydroxybenzoyl)-benzofuran.

Workup

  1. additionA mixture of 10.0 g
  2. extractionextracted with chloroform
  3. washThe extracts were washed repeatedly with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f514e21602dc49bba1158051335f98e8
Source dataset
uspto-grants-1976_08
Patent number
US03975537

Reaction notes

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