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

HRID 991597Notes

Reaction equation

HRID 991597 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 were water and petroleum ether 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 title product. (3.7 g, 43%)

Workup

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

Sources & evidence

ORD record
ord-7934c249121241f8928c1c0ff8e263e2
Source dataset
uspto-grants-2002_10
Patent number
US06465505B1

Reaction notes

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