Hydrogen Bromide → (3-Bromo-2-methylphenyl)methanol

HRID 1656926Notes

Reaction equation

HRID 1656926 reaction equation
[N+]([O-])([O-])=O.[Na+].[BrH:6].N[C:8]1[C:9]([CH3:16])=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11][OH:12]>O.[Cu]Br>[Br:6][C:8]1[C:9]([CH3:16])=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11][OH:12]

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 24268Sodium NitrateHCID 577175(3-Amino-2-methylphenyl)methanol

Product 1

HCID 10035697(3-Bromo-2-methylphenyl)methanol

Reagents, catalysts & solvents 2

HCID 24593copper(I) bromideCatalystHCID 962WaterSolvent3×

Procedure

A solution of 40.7 g of sodium nitrate in 300 ml of water is added dropwise to a mixture, cooled to 0° C., of 888 ml of water, 162 ml of 47% hydrobromic acid and 81.2 g of 3-amino-2-methylbenzyl alcohol. Stirring is carried out for 30 minutes at 0° C., after which a suspension of 168.7 9 of copper(I) bromide in 750 ml of water is added a little at a time at this temperature. The reaction mixture is stirred in succession for 1 hour at 10° C., for 1 hour at room temperature and for 2 hours at 100° C. After cooling, the reaction mixture is extracted several times with ether. The combined organic phases are washed with water, dried and evaporated down. Purification by column chromatogrpahy over silica gel using toluene as the mobile phase gives 64.2 g of 3-bromo-2-methylbenzyl alcohol (mp. 97°-100° C.).

Workup

  1. additionis added a little at a time at this temperature
  2. stirringThe reaction mixture is stirred in succession for 1 hour at 10° C., for 1 hour at room temperature and for 2 hours at 100° C
  3. temperatureAfter cooling
  4. extractionthe reaction mixture is extracted several times with ether
  5. washThe combined organic phases are washed with water
  6. customdried
  7. customevaporated down
  8. customPurification by column chromatogrpahy over silica gel

Sources & evidence

ORD record
ord-192d1e9365bb4f67af3bf72ef036cb13
Source dataset
uspto-grants-1993_10
Patent number
US05256666

Reaction notes

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