o-Vanillin → 5-Bromo-2-hydroxy-3-methoxybenzaldehyde

HRID 855068Notes

Reaction equation

HRID 855068 reaction equation
[OH:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[Br:12]Br>C(O)(=O)C.O>[Br:12][C:7]1[CH:8]=[C:9]([O:10][CH3:11])[C:2]([OH:1])=[C:3]([CH:6]=1)[CH:4]=[O:5]

Participants

5

Reactant 2

HCID 8991o-VanillinHCID 24408Bromine

Product 1

HCID 2622385-Bromo-2-hydroxy-3-methoxybenzaldehydeYield 80.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

The solution of 2-hydroxy-3-methoxybenzaldehyde (10.0 g, 65.79 mmole) in acetic acid (50 mL) was cooled to 0° C. (ice bath). Bromine (12.55 g, 78.95 mmole) was added dropwise to above solution, which was allowed to stir for 2 hours. The reaction was warmed to room temperature and diluted with water (100 mL). A light brown precipitate was formed. The solid was filtered and washed with water (50 mL). The filtrate was dried on high vacuum to give a light brown solid (12.2 g, 80.0%): GCMS m/z 231.0 (M+). 1H NMR (CDCl3/400 MHz) 10.97 (s, 1H), 9.82 (s, 1H), 7.29 (s, 1H), 7.15 (s, 1H), 3.89 (m, 3H).

Workup

  1. customA light brown precipitate was formed
  2. filtrationThe solid was filtered
  3. washwashed with water (50 mL)
  4. customThe filtrate was dried on high vacuum

Sources & evidence

ORD record
ord-cb60c76288974d7493c710d5463941d9
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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