3-Hydroxybenzaldehyde → 2-Bromo-5-hydroxybenzaldehyde

HRID 1181036Notes

Reaction equation

HRID 1181036 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[Br:10]Br>C(Cl)Cl>[Br:10][C:7]1[CH:8]=[CH:9][C:2]([OH:1])=[CH:3][C:4]=1[CH:5]=[O:6]

Participants

4

Reactant 2

HCID 1013-HydroxybenzaldehydeHCID 24408Bromine

Product 1

HCID 3871792-Bromo-5-hydroxybenzaldehydeYield 63.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 3-hydroxybenzaldehyde (1 kg, 8.2 mol) in CH2Cl2 (10 L) was added a solution of bromine (1.3 kg, 8.2 mol) in CH2Cl2 (620 mL) over 1 h. After stirring for about 22 h, the solids were isolated by filtration, washed with CH2Cl2 (4 L), and dried under vacuum to afford of 2-bromo-5-hydroxybenzaldehyde as a tan solid (1.05 kg, 63%).

Workup

  1. customthe solids were isolated by filtration
  2. washwashed with CH2Cl2 (4 L)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-af67694d474546d6825e80924afe9f47
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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