Hydrogen Bromide → 2-(4-Bromophenethyl)-benzyl bromide

HRID 1288544Notes

Reaction equation

HRID 1288544 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][CH2:7][C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[CH2:10]O)=[CH:4][CH:3]=1.[BrH:18]>>[Br:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][CH2:7][C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[CH2:10][Br:18])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 543373022-(4-Bromophenethyl)-benzyl alcohol

Product 1

HCID 215028812-(4-Bromophenethyl)-benzyl bromide

Procedure

A suspension of 28.5 g. (0.098 mole) of 2-(4-bromophenethyl)-benzyl alcohol in 150 ml. of 48% hydrobromic acid is stirred at reflux for 3 hours. The cooled two-phase mixture is extracted with benzene. Evaporation of the washed and dried benzene extract under reduced pressure leaves the product as the residual solid, m.p. 63°-75° C. Recrystallization from hexane affords purified material, m.p. 76°-77.5° C. A sample for analysis melts at 76.5°-78° C. after further recrystallization from hexane.

Workup

  1. additionA suspension of 28.5 g
  2. temperatureat reflux for 3 hours
  3. extractionThe cooled two-phase mixture is extracted with benzene
  4. customEvaporation of the
  5. washwashed
  6. extractiondried benzene extract under reduced pressure
  7. customleaves the product as the residual solid, m.p. 63°-75° C
  8. customRecrystallization from hexane
  9. customaffords
  10. custompurified material, m.p. 76°-77.5° C
  11. customA sample for analysis melts at 76.5°-78° C. after further recrystallization from hexane

Sources & evidence

ORD record
ord-73b9c40b456d4eeaae413c939f083d61
Source dataset
uspto-grants-1976_10
Patent number
US03988454

Reaction notes

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