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

HRID 705699Notes

Reaction equation

HRID 705699 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 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3-chloro-4-hydroxy-5-methoxy-benzaldehyde (36.0 g, 193 mmol) in dichloromethane (1000 mL) was added BBr3 (97.0 g, 387 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 solid was dried under reduced pressure to afford the title compound (30.0 g; 91%), 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 solid was dried under reduced pressure

Sources & evidence

ORD record
ord-cfb28b68ec1740b89748dfbeb090723f
Source dataset
uspto-grants-2015_11
Patent number
US09174967B2

Reaction notes

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