Potassium Carbonate → 4-Bromobenzaldehyde

HRID 2306500Notes

Reaction equation

HRID 2306500 reaction equation
BrCC1C=CC(C2SC([C:14]([C:16]3[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=3)=[O:15])=CC=2)=CC=1.C(=O)([O-])[O-].[K+].[K+].C(NC)C=C>CC(C)=O>[Br:22][C:19]1[CH:20]=[CH:21][C:16]([CH:14]=[O:15])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 69391N-MethylallylamineHCID 18434203HCID 18434203, compound

Product 1

HCID 707414-Bromobenzaldehyde

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

435 mg of [5-(4-bromomethyl-phenyl)-thiophen-2-yl]-4-bromophenyl-methanone are dissolved in 25 ml of acetone, 300 mg of potassium carbonate and 0.15 ml of N-allyl-methyl-amine are added and the mixture is held at reflux under argon for 4 hrs., treated with ice-water, extracted with ethyl acetate, dried and chromatographed on silica gel (ethyl acetate/hexane). 219 mg of 5-(4-[(allyl-methylamino)-methyl]-phenyl)-thiophen-2-yl)-(4-bromphenyl)-methanone, m.p. 131-133° C., are isolated.

Workup

  1. temperatureat reflux under argon for 4 hrs
  2. extractionextracted with ethyl acetate
  3. customdried
  4. customchromatographed on silica gel (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-77f033c3115246149eee4094e4870892
Source dataset
uspto-grants-2002_08
Patent number
US06441177B1

Reaction notes

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