Boron tribromide → 4-Fluoro-3-hydroxybenzaldehyde

HRID 2105037Notes

Reaction equation

HRID 2105037 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10]C.B(Br)(Br)Br>C(Cl)Cl>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[OH:10]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 27373584-Fluoro-3-methoxybenzaldehyde

Product 1

HCID 5877924-Fluoro-3-hydroxybenzaldehydeYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-fluoro-3-methoxybenzaldehyde (1.5 g, 10 mmol), 10 mL CH2Cl2 at 0° C., was added BBr3 (30 mL, 1N, 30 mmol) dropwise. The mixture was allowed to warn up to rt over 1 h, then quenched with ice water and diluted with EtOAc. The organic phase was washed with sat. NaHCO3 and brine, dried (Na2SO4), filtered and concentrated. The crude product was purified by flash chromatography (0 to 5% EtOAc/hexanes, gradient) to afford 1.2 mg (85%) of Intermediate 255.1.

Workup

  1. customquenched with ice water
  2. additiondiluted with EtOAc
  3. washThe organic phase was washed with sat. NaHCO3 and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography (0 to 5% EtOAc/hexanes, gradient)

Sources & evidence

ORD record
ord-b7c2b9668de14c8999d69432e93c3aac
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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