Bromine → 4-Bromo-2,6-difluorophenol

HRID 477412Notes

Reaction equation

HRID 477412 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[OH:9].[Br:10]Br.S(=O)(O)[O-].[Na+]>C(Cl)Cl.[Fe]>[Br:10][C:6]1[CH:7]=[C:2]([F:1])[C:3]([OH:9])=[C:4]([F:8])[CH:5]=1

Participants

6

Reactant 3

HCID 24408BromineHCID 943922,6-DifluorophenolHCID 23665763Sodium Bisulfite

Product 1

HCID 27362924-Bromo-2,6-difluorophenol

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 6344DichloromethaneSolvent

Procedure

A stirred mixture of 2,6-difluorophenol (20.0 g, 0.154 mole), bromine (25.57 g, 0.16 mole) and powdered iron (1 g) in methylene chloride (250 ml) was heated at reflux overnight. The cooled reaction mixture was poured into ice-water (300 ml) containing sodium bisulfite (5 g) and the organic phase separated. The aqueous phase was washed with additional methylene chloride. The organic phase was combined, dried (MgSO4) and the solvent evaporated to give a light yellow oil which solidified upon standing. NMR (CDCL3) of this material was consistent with the assigned structure. No additional analysis or purification was attempted. This material was used directly in the next step.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customThe cooled reaction mixture
  4. customthe organic phase separated
  5. washThe aqueous phase was washed with additional methylene chloride
  6. dry with materialdried (MgSO4)
  7. customthe solvent evaporated
  8. customto give a light yellow oil which
  9. customNo additional analysis or purification

Sources & evidence

ORD record
ord-80667c6a1fa5420e9153b1176459e1ce
Source dataset
uspto-grants-1989_12
Patent number
US04888050

Reaction notes

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