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

HRID 1991639Notes

Reaction equation

HRID 1991639 reaction equation
[Cl: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>[Cl: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 296223-Chloro-4-hydroxy-5-methoxybenzaldehyde

Product 1

HCID 24681823-Chloro-4,5-dihydroxybenzaldehydeYield 105.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3-chloro-4-hydroxy-5-methoxy-benzaldehyde (10 g, 54 mmol) in dichloromethane (300 mL) was added BBr3 (26.7 g, 107 mmol) dropwise at −40° C. under N2. After addition, the mixture was stirred at this temperature for 5 h and then was poured into ice water. The precipitated solid was filtered and washed with petroleum ether. The filtrate was evaporated under reduced pressure to afford 3-chloro-4,5-dihydroxybenzaldehyde (9.8 g, 89%), which was directly used in the next step.

Workup

  1. additionAfter addition
  2. filtrationThe precipitated solid was filtered
  3. washwashed with petroleum ether
  4. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-036b0f40554f494c9e351b6773901c01
Source dataset
uspto-grants-2010_01
Patent number
US07645789B2

Reaction notes

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