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

HRID 468243

Reaction equation

HRID 468243 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([O:10]C)[C:7]([O:12]C)=[CH:6][C:3]=1[CH:4]=[O:5].B(Br)(Br)Br>ClCCl>[F:1][C:2]1[CH:9]=[C:8]([OH:10])[C:7]([OH:12])=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

4

Reactant 2

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

Product 1

HCID 5933632-Fluoro-4,5-dihydroxybenzaldehydeYield 314.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-30 °C

Procedure

To a stirred suspension of 2-fluoro-4,5-dimethoxy-benzaldehyde (3.00 g, 16.3 mmol) in dichloromethane (100 mL) was added BBr3 (12.2 mL, 130 mmol) dropwise at −78° C. under nitrogen atmosphere. After addition, the mixture was warmed to −30° C. and stirred at this temperature for 5 h. The reaction mixture was poured into ice water and the precipitated solid was collected by filtration and washed with dichloromethane to afford 2-fluoro-4,5-dihydroxy-benzaldehyde (8.0 g), which was used directly in the next step.

Workup

  1. additionAfter addition
  2. filtrationthe precipitated solid was collected by filtration
  3. washwashed with dichloromethane

Sources & evidence

ORD record
ord-75f4d33c74344e3b87dff540107f8c06
Source dataset
uspto-grants-2014_01
Patent number
US08623905B2

Linked notes

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