Phenol, 2-fluoro-5-methyl- → 4-Bromo-2-fluoro-5-methylphenol

HRID 407981Notes

Reaction equation

HRID 407981 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-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)(Cl)Cl>[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 182387Phenol, 2-fluoro-5-methyl-HCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 108997434-Bromo-2-fluoro-5-methylphenolYield 96%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-Fluoro-5-methylphenol (5.0 g, 40 mmol) was dissolved in chloroform (200 mL). Tetrabutylammonium tribromide (19 g, 40 mmol) was added and the reaction stirred at ambient temperature for 30 minutes. The reaction was concentrated and purified over silica gel (20% EtOAc in hexanes) to afford 4-bromo-2-fluoro-5-methylphenol (7.8 g, 38 mmol, 96% yield) as an amber oil.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified over silica gel (20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-9bc38907ef0b4dfca8248dd9330b26ec
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

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