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

HRID 15307

Reaction equation

HRID 15307 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 14.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-fluoro-4-hydroxy-5-(methyloxy)benzaldehyde (5.0 g, 29.4 mmol) in dichloromethane (80 ml) at 0° C. was added boron tribromide (43 ml, 1M solution in dichloromethane) dropwise and then the reaction was allowed to stir for 1 h at rt before the solvent was removed under reduced pressure and the residue acidified with aqueous HCl (1M). The resultant solid was filtered, washed with water and dried in vacuo to give the desired compound (0.66 g, 14%).

Workup

  1. customwas removed under reduced pressure
  2. filtrationThe resultant solid was filtered
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-4c41217c3547423eb3c49cdf8fa1846b
Source dataset
uspto-grants-2010_06
Patent number
US07732461B2

Linked notes

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