Benzyl Bromide → 6-(Benzyloxy)-2,3-difluorobenzaldehyde

HRID 573194Notes

Reaction equation

HRID 573194 reaction equation
[F:1][C:2]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([OH:11])[C:3]=1[CH:4]=[O:5].Br[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:13]([O:11][C:6]1[C:3]([CH:4]=[O:5])=[C:2]([F:1])[C:9]([F:10])=[CH:8][CH:7]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 212210312,3-Difluoro-6-hydroxybenzaldehyde

Product 1

HCID 534408986-(Benzyloxy)-2,3-difluorobenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2,3-difluoro-6-hydroxybenzaldehyde (0.93 g), (bromomethyl)benzene (1.11 g) and potassium carbonate (1.22 g) in N,N-dimethylformamide (15 mL) was heated at 70° C. overnight. After cooling to room temperature, the reaction mixture was partitioned between water and ethyl acetate. The organic layer was separated, and the aqueous layer was extracted with additional ethyl acetate three times. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography on silica gel to give the title compound.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe reaction mixture was partitioned between water and ethyl acetate
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with additional ethyl acetate three times
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-7592ce922fe84e32838834e107e0bb33
Source dataset
uspto-grants-2015_05
Patent number
US09029404B2

Reaction notes

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