Acetic Acid → 2-(Bromomethyl)-5-fluoro-1,3-dimethylbenzene

HRID 1006686Notes

Reaction equation

HRID 1006686 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([F:9])[CH:5]=[C:6](C)[CH:7]=1.C=O.[BrH:12].[C:13](O)(=O)[CH3:14]>O>[CH3:1][C:2]1[CH:3]=[C:4]([F:9])[CH:5]=[C:13]([CH3:14])[C:7]=1[CH2:6][Br:12]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 712FormaldehydeHCID 5211921-Fluoro-3,5-dimethyl-benzene

Product 1

HCID 226726412-(Bromomethyl)-5-fluoro-1,3-dimethylbenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3,5-dimethyl-fluorobenzene (5 g, 0.04 mol), paraformaldehyde (15 g), hydrobromic acid (70 ml) (30% in acetic acid) and acetic acid (25 ml) was stirred at ambient temperature for 4.5 h. To the mixture, water and petroleum ether were added and the organic layer was separated dried over anhydrous sodium sulfate and evaporated carefully under reduced pressure. The residue was purified by column chromatography on silica gel with petroleum ether as eluent to give the desired product. (3.7 g, 43%).

Workup

  1. customthe organic layer was separated
  2. dry with materialdried over anhydrous sodium sulfate
  3. customevaporated carefully under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel with petroleum ether as eluent

Sources & evidence

ORD record
ord-23a3218e1d904a0c8b0077dd5a361a72
Source dataset
uspto-grants-2004_09
Patent number
US06790960B2

Reaction notes

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