Water → 5-Bromo-3,4-dihydroxybenzaldehyde

HRID 1677295Notes

Reaction equation

HRID 1677295 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].[Br:11]Br.O>CC(O)=O>[Br:11][C:8]1[CH:7]=[C:4]([CH:3]=[C:2]([OH:1])[C:9]=1[OH:10])[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 87683,4-DihydroxybenzaldehydeHCID 24408Bromine

Product 1

HCID 854055-Bromo-3,4-dihydroxybenzaldehydeYield 447%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 3,4-dihydroxy benzaldehyde (115.48 g, 12 mmol) in 500 ml AcOH was added bromine (6.1 ml, 118 mmol) drop-wise in 50 ml AcOH over 10 min. After 4 h the mixture was poured into cold H2O. The precipitate was filtered, washed with cold H2O and dried in vacuum to give 3-bromo-4,5-dihydroxy-benzaldehyde (11.64 g, 48%) as a grey solid.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with cold H2O
  3. customdried in vacuum

Sources & evidence

ORD record
ord-f1116e151f904fb8884400d20a7c6a3c
Source dataset
uspto-grants-2011_08
Patent number
US08008313B2

Reaction notes

Loading…