2-Bromophenol → HCID 86627407, compound

HRID 1686141Notes

Reaction equation

HRID 1686141 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:9]=1)[CH:7]=[O:8].[Br:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[OH:18].C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[Br:11])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

6

Reactant 3

HCID 72442-BromophenolHCID 11430Potassium CarbonateHCID 7363275-Bromo-2-fluorobenzaldehyde

Product 1

HCID 86627407HCID 86627407, compoundYield 46.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 5-bromo-2-fluorobenzaldehyde (0.203 g, 1 mmol) in DMA (2.5 mL) were added 2-bromophenol (0.182 g, 1.05 mmol) and potassium carbonate (0.138 g, 1 mmol), followed by stirring at 120° C. for 12 hours. The reaction solution was diluted with ethyl acetate, washed with brine, dried over MgSO4, and concentrated. The residue was purified through column chromatography (20% ethyl acetate/hexane) and concentrated to obtain the object compound (0.164 g, 46%).

Workup

  1. washwashed with brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified through column chromatography (20% ethyl acetate/hexane)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ed2b02ba847947b3a54f868b25cef027
Source dataset
uspto-grants-2012_04
Patent number
US08148541B2

Reaction notes

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