3-Hydroxybenzyl alcohol → 3-(Bromomethyl)phenol

HRID 557477Notes

Reaction equation

HRID 557477 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.ClCCl.C(Br)(Br)(Br)[Br:14]>C(#N)C>[Br:14][CH2:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 1023-Hydroxybenzyl alcoholHCID 6344DichloromethaneHCID 11205Carbon tetrabromide

Product 1

HCID 137401503-(Bromomethyl)phenol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
2.5 °C

Procedure

3-[(Hydroxy)methyl]phenol was dissolved in acetonitrile (300 ml) and dichloromethane (900 ml) and the resulting mixture was poured in the flask kept under argon; magnetic stirring was set on. The solution was then cooled with an ice bath and carbon tetrabromide and triphenilphosphine were added. The latter was added in small portions in order to maintain the temperature at ca. 2-3° C.

Workup

  1. temperatureThe solution was then cooled with an ice bath
  2. additionThe latter was added in small portions in order

Sources & evidence

ORD record
ord-6340273e495540a2a249a1b796f18893
Source dataset
uspto-grants-2011_11
Patent number
US08058467B2

Reaction notes

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