Bromine → 5-bromo-2-hydroxy-3-methylbenzaldehyde

HRID 855097Notes

Reaction equation

HRID 855097 reaction equation
[OH:1][C:2]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[Br:11]Br>C(O)(=O)C.O>[Br:11][C:7]1[CH:8]=[C:9]([CH3:10])[C:2]([OH:1])=[C:3]([CH:6]=1)[CH:4]=[O:5]

Participants

5

Reactant 2

HCID 24408BromineHCID 5227773-Methylsalicylaldehyde

Product 1

HCID 27570165-bromo-2-hydroxy-3-methylbenzaldehydeYield 88.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

The solution of 2-Hydroxy-3-methylbenzaldehyde (1.0 g, 7.35 mmole) in acetic acid (6 mL) was cooled to 0° C. (ice bath). Bromine (1.36 g, 8.52 mmole) was added dropwise and allowed to stir for 2 hours. The reaction was warmed to room temperature and diluted with water (100 mL) yielding a light orange precipitate. The solid was filtered and washed with water (10 mL). Dried on high vacuum to give a light brown solid (1.4 g, 88.6%). 1H NMR (CDCl3/400 MHz) 11.16 (s, 1H), 9.79 (s, 1H), 7.48 (s, 1H), 7.46 (s, 1H), 2.23 (s, 3H).

Workup

  1. customyielding a light orange precipitate
  2. filtrationThe solid was filtered
  3. washwashed with water (10 mL)
  4. customDried on high vacuum

Sources & evidence

ORD record
ord-2129189d30cf43e9beacb6550c373296
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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