Potassium Carbonate → 3-Bromo-4-(4-formyl-phenoxy)-benzamide

HRID 492565Notes

Reaction equation

HRID 492565 reaction equation
C([O-])([O-])=O.[K+].[K+].F[C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=1.[Br:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][C:25]=1[OH:26])[C:20]([NH2:22])=[O:21]>CN(C=O)C>[Br:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][C:25]=1[O:26][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=1)[C:20]([NH2:22])=[O:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 680234-FluorobenzaldehydeHCID 151699323-Bromo-4-hydroxybenzamide

Product 1

HCID 597301703-Bromo-4-(4-formyl-phenoxy)-benzamideYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add K2CO3 (1.49 g, 10.8 mmol) to a solution of 4-fluorobenzaldehyde (1.16 mL, 10.8 mmol) and 3-bromo-4-hydroxy-benzamide (1.16 g, 5.4 mmol) in DMF (20 mL). Heat the mixture under N2 overnight. Cool the mixture at room temperature and pour it into ice-water. Extract the aqueous layer with EtOAc. Dry the organic layer over Na2SO4. Eliminate the solvent. Purify by flash chromatography (eluent: EtOAc/hexane 2/1 and 4/1) to get the title compound (1.0 g, 58%). 1H-NMR (metanol-d4, 300 MHz): 9.84 (s, 1H), 8.18 (d, 1H, J=2.0 Hz), 7.88-7.83 (m, 3H), 7.13 (d, 1H, J=8.5 Hz), 7.04-7.01 (m, 2H).

Workup

  1. temperatureHeat the mixture under N2 overnight
  2. extractionExtract the aqueous layer with EtOAc
  3. dry with materialDry the organic layer over Na2SO4
  4. customPurify by flash chromatography (eluent: EtOAc/hexane 2/1 and 4/1)

Sources & evidence

ORD record
ord-1b8fa97c23064116a5b8f6a500936b7b
Source dataset
uspto-grants-2009_05
Patent number
US07531557B2

Reaction notes

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