Boron tribromide → 2-Fluoro-4,5-dihydroxybenzaldehyde

HRID 2103120Notes

Reaction equation

HRID 2103120 reaction equation
[F:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][C:5]([O:10]C)=[C:4]([O:12]C)[CH:3]=1.B(Br)(Br)Br>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([OH:12])[C:5]([OH:10])=[CH:6][C:7]=1[CH:8]=[O:9]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 6035952-Fluoro-4,5-dimethoxybenzaldehyde

Product 1

HCID 5933632-Fluoro-4,5-dihydroxybenzaldehydeYield 0.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cooled (−78° C.) solution of 6-fluoroveratraldehyde (2 g, 10.9 mmol) in dichloromethane (40 mL) was added a solution of boron tribromide in dichloromethane (1M, 44 mL, 44 mmol, 4.0 eq.). The reaction was allowed to reach room temperature and was stirred overnight. The reaction mixture was partitioned between ice water and diethyl ether. The aqueous layer was extracted with diethyl ether. The combined organic layer was washed with water dried over sodium sulfate and filtered. Volatiles were removed in vacuo. Purification by flash chromatography afforded the title compound (1.71 mg, quant.) as a dark solid

Workup

  1. customto reach room temperature
  2. customThe reaction mixture was partitioned between ice water and diethyl ether
  3. extractionThe aqueous layer was extracted with diethyl ether
  4. washThe combined organic layer was washed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customVolatiles were removed in vacuo
  8. customPurification by flash chromatography

Sources & evidence

ORD record
ord-a94de26cb3964792b210eaa01f294a73
Source dataset
uspto-grants-2009_08
Patent number
US07576088B2

Reaction notes

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