2-Bromophenol → 4-(2-Bromophenoxy)benzaldehyde

HRID 1823951Notes

Reaction equation

HRID 1823951 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[Br:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[OH:17].C(=O)([O-])[O-].[K+].[K+].CN(C)C(=O)C>O>[Br:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 72442-BromophenolHCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 680234-Fluorobenzaldehyde

Product 1

HCID 131696974-(2-Bromophenoxy)benzaldehydeYield 37.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

To a mixture of 4-fluorobenzaldehyde (2.5 g, 20.2 mmol), 2-bromophenol (3.5 g, 20.2 mmol) and potassium carbonate (3.35 g, 24.3 mmol) is added N,N-dimethylacetamide (20 mL) and the resulting reaction mixture is heated to 150° C. for 12 hours. Once complete, the reaction is cooled to room temperature and diluted with water prior to being extracted with ethyl acetate. The combined extracts are washed with brine and dried over sodium sulfate and concentrated. The resulting yellow oil is purified by column chromatography (5% ethyl acetate in hexanes) to afford 2.1 g of 4-(2-bromophenoxy)benzaldehyde.

Workup

  1. customthe resulting reaction mixture
  2. temperatureOnce complete, the reaction is cooled to room temperature
  3. extractionto being extracted with ethyl acetate
  4. washThe combined extracts are washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe resulting yellow oil is purified by column chromatography (5% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-daab37f2d9fe4fbfa45aa1df2bc86e5a
Source dataset
uspto-grants-2006_05
Patent number
US07041690B2

Reaction notes

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