Boron tribromide → 3-Fluoro-4,5-dihydroxybenzaldehyde

HRID 39144Notes

Reaction equation

HRID 39144 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:11]C)[C:9]=1[OH:10])[CH:5]=[O:6].B(Br)(Br)Br>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:11])[C:9]=1[OH:10])[CH:5]=[O:6]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 5984523-Fluoro-4-hydroxy-5-methoxybenzaldehyde

Product 1

HCID 5936643-Fluoro-4,5-dihydroxybenzaldehydeYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-30 °C

Procedure

To a suspension of 3-fluoro-4-hydroxy-5-methoxy-benzaldehyde (1.35 g, 7.94 mmol) in dichloromethane (100 mL) was added BBr3 (1.5 mL, 16 mmol) dropwise at −78° C. under N2. After addition, the mixture was warmed to −30° C. and it was stirred at this temperature for 5 h. The reaction mixture was poured into ice water. The precipitated solid was collected by filtration and washed with dichloromethane to afford 3-fluoro-4,5-dihydroxy-benzaldehyde (1.1 g, 89%), which was directly used 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-8469dc88f312436c81456e29da631f3e
Source dataset
uspto-grants-2013_09
Patent number
US08524767B2

Reaction notes

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