Bromine → 4-Bromo-2-fluoro-5-methylphenol

HRID 1851633Notes

Reaction equation

HRID 1851633 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[OH:9].[Br:10]Br>C(O)(=O)C>[Br:10][C:6]1[C:5]([CH3:8])=[CH:4][C:3]([OH:9])=[C:2]([F:1])[CH:7]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 182387Phenol, 2-fluoro-5-methyl-

Product 1

HCID 108997434-Bromo-2-fluoro-5-methylphenolYield 98%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-fluoro-5-methylphenol (23.8 g, 0.19 mol) and bromine (9.7 ml, 0.19 mol) are combined in 50 ml of glacial acetic acid and stirred at RT for one hour. Acetic acid was removed under vacuum. The liquid was diluted with ethyl acetate and washed with water. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to afford 4-bromo-2-fluoro-5-methylphenol (38 g, 98% yield) as a colorless liquid. No [M+H] peak by LCMS. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.98 (s, 1 H) 2.22 (s, 3 H) 6.81 (dd, J=9.15, 0.54 Hz, 1 H) 7.17 (d, J=9.88 Hz, 1 H)

Workup

  1. customAcetic acid was removed under vacuum
  2. additionThe liquid was diluted with ethyl acetate
  3. washwashed with water
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f3eaf125f0d349b684003001b8058f5a
Source dataset
uspto-grants-2015_02
Patent number
US08957083B2

Reaction notes

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