Water → 3-Bromo-5-fluoro-4-hydroxybenzaldehyde

HRID 401209Notes

Reaction equation

HRID 401209 reaction equation
[F: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>C(O)(=O)C.ClCCl>[Br:11][C:8]1[CH:7]=[C:4]([CH:3]=[C:2]([F:1])[C:9]=1[OH:10])[CH:5]=[O:6]

Participants

6

Reactant 3

HCID 962WaterHCID 24408BromineHCID 5872503-Fluoro-4-hydroxybenzaldehyde

Product 1

HCID 187017503-Bromo-5-fluoro-4-hydroxybenzaldehydeYield 64%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a mixture of 3-fluoro-4-hydroxybenzaldehyde (700 mg, 5.0 mmol) in acetic acid (5 mL) and dichloromethane (5 mL) was added bromine (0.5 mL, 9.8 mmol) at 0° C. The resulting mixture was stirred at 20° C. for 7 hours and then it was poured into water (50 mL), filtrated, the filtered cake was dried to give Intermediate 77 (700 mg, yield 64%).

Workup

  1. filtrationfiltrated
  2. customthe filtered cake was dried

Sources & evidence

ORD record
ord-05676e4fead34968a95bb73a851d888d
Source dataset
uspto-grants-2014_06
Patent number
US08741915B2

Reaction notes

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