Hydrogen Bromide → 2-Bromo-5-methoxybenzyl bromide

HRID 1270783Notes

Reaction equation

HRID 1270783 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([Br:11])=[C:7]([CH:10]=1)[CH2:8]O.O.[BrH:13]>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([Br:11])=[C:7]([CH:10]=1)[CH2:8][Br:13]

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 10867706(2-Bromo-5-methoxyphenyl)methanol

Product 1

HCID 35259512-Bromo-5-methoxybenzyl bromide

Procedure

5-Methoxy-2-bromobenzyl alcohol (79.5 g, 0.37 mol) is dissolved in 48% HBr (400 mL) and heated to reflux temperature for 4 hours. The reaction mixture is cooled to room temperature and poured into water (1500 mL). The solution is extracted with EtOAc (2×500 mL). The combined organic layers are dried (MgSO4) and concentrated by rotary evaporator. The crude material is then purified using flash chromatography (CH2Cl2/hexanes, from 1:1 to 4:1) to give 5-methoxy-2-bromobenzyl bromide.

Workup

  1. temperatureheated
  2. temperatureto reflux temperature for 4 hours
  3. extractionThe solution is extracted with EtOAc (2×500 mL)
  4. dry with materialThe combined organic layers are dried (MgSO4)
  5. concentrationconcentrated by rotary evaporator
  6. customThe crude material is then purified

Sources & evidence

ORD record
ord-2bad3c1398894d8787aa73b06d3eec34
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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