Water → 4-Bromo-2-fluorophenol

HRID 1761939Notes

Reaction equation

HRID 1761939 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[Br:9]Br.O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(=S)=S>[F:1][C:2]1[CH:7]=[C:6]([Br:9])[CH:5]=[CH:4][C:3]=1[OH:8]

Participants

6

Procedure

2-Fluorophenol (56.03 g) was dissolved in carbon disulphide (100 ml). A solution of bromine (87.89 g) in carbon disulphide (30 ml) was added dropwise over a period of 5 hours with vigorous stirring. The mixture was allowed to stand overnight at room temperature, then was poured into water (80 ml). A saturated solution of sodium thiosulphate (200 ml) was added and the mixture shaken. The organic layer was separated, washed with saturated sodium bicarbonate solution (100 ml) and water (150 ml). The organic layer was dried over anhydrous sodium sulphate, then was evaporated to leave 2-fluoro-4-bromophenol as an orange oil. This was distilled at about 14 mm Hg pressure. The fractions distilling at 89°-92° C. (65 g 98% pure by g.l.c.) and 92°-96° C. (10 g 97% pure by g.l.c.) were collected.

Workup

  1. customThe organic layer was separated
  2. washwashed with saturated sodium bicarbonate solution (100 ml) and water (150 ml)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  4. customwas evaporated

Sources & evidence

ORD record
ord-d486cb0c54a740c5868b007f5401ac51
Source dataset
uspto-grants-1989_05
Patent number
US04829074

Reaction notes

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