Water → 4-Bromo-5-[(3-methoxyphenyl)thio]thiophene-2-carbaldehyde

HRID 2194671

Reaction equation

HRID 2194671 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[O:9])[S:5][C:6]=1Br.C(=O)([O-])[O-].[K+].[K+].[CH3:16][O:17][C:18]1[CH:19]=[C:20]([SH:24])[CH:21]=[CH:22][CH:23]=1.O>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[O:9])[S:5][C:6]=1[S:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([O:17][CH3:16])[CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 849893-MethoxybenzenethiolHCID 8131644,5-Dibromothiophene-2-carbaldehyde

Product 1

HCID 866315874-Bromo-5-[(3-methoxyphenyl)thio]thiophene-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4,5-dibromothiophene-2-carbaldehyde (1.0 g) in N,N-dimethylformamide (10 mL) were added potassium carbonate (665 mg) and 3-methoxybenzenethiol (571 mg) at room temperature. After stirring at room temperature overnight, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→7:1) to give the title compound as a pale-yellow crude oil (yield 1.30 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→7:1)

Sources & evidence

ORD record
ord-42044a88884941bb851bb2346bbbdb37
Source dataset
uspto-grants-2012_12
Patent number
US08334301B2

Linked notes

Loading…