Phosphorus tribromide → 1-Bromo-4-propylcyclohexane

HRID 1707526

Reaction equation

HRID 1707526 reaction equation
[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7](O)[CH2:6][CH2:5]1)[CH2:2][CH3:3].P(Br)(Br)[Br:12]>>[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7]([Br:12])[CH2:6][CH2:5]1)[CH2:2][CH3:3]

Participants

3

Procedure

142 g (1.0 mol) of 4-propylcyclohexanol (trans-cis form mixture) was given drop addition of 136 g (0.5 mol) of PBr3 while stirring at room temperature, and heated to about 80° C. The reactant was stirred for 1 hour on a 70° C. hot water bath, then cooled to room temperature and poured into ice water to decompose the excess PBr3. The oily layer was taken off, and the water layer was extracted with chloroform, combined with the oily layer and washed with water. The chloroform was removed, and the remaining oily substance was distilled under reduced pressure (b. p. 97° C./14 mmHg) to obtain 180 g (0.88 mol) of 4-propylbromocyclohexane (trans-cis form mixture).

Workup

  1. temperatureheated to about 80° C
  2. stirringThe reactant was stirred for 1 hour on a 70° C. hot water bath
  3. temperaturecooled to room temperature
  4. extractionthe water layer was extracted with chloroform
  5. washwashed with water
  6. customThe chloroform was removed
  7. distillationthe remaining oily substance was distilled under reduced pressure (b. p. 97° C./14 mmHg)

Sources & evidence

ORD record
ord-923e4ed5e81443bda5cbfe3b717fda98
Source dataset
uspto-grants-1994_10
Patent number
US05354502

Linked notes

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