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

HRID 1386080Notes

Reaction equation

HRID 1386080 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 desired 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-c6e3ce953a9c42a2b27a7a66441c55d1
Source dataset
uspto-grants-2001_07
Patent number
US06265415B1

Reaction notes

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