Phosphorus tribromide → 4-(Bromomethyl)heptane

HRID 1883973Notes

Reaction equation

HRID 1883973 reaction equation
P(Br)(Br)[Br:2].[CH2:5]([CH:8]([CH2:11][CH2:12][CH3:13])[CH2:9]O)[CH2:6][CH3:7]>>[Br:2][CH2:9][CH:8]([CH2:11][CH2:12][CH3:13])[CH2:5][CH2:6][CH3:7]

Participants

3

Procedure

Phosphorus tribromide (33.3 g, 0.123 mol) was added dropwise to 2-propyl-1-pentanol (40 g, 0.307 mol) at −10° C. to maintain the temperature below 0° C. and the mixture was stirred overnight at room temperature. The reaction mixture was heated at 100° C. for 1 h, cooled to room temperature, and poured into ice water (250 ml). The organic layer was separated, washed with conc. H2SO4 (25 ml) followed by saturated K2CO3 (25 ml), dried and distilled in vacuo (80° C./15 mm Hg) to furnish 40 g (83%) of 1-bromo-2-propylpentane.

Workup

  1. temperatureto maintain the temperature below 0° C.
  2. temperatureThe reaction mixture was heated at 100° C. for 1 h
  3. temperaturecooled to room temperature
  4. customThe organic layer was separated
  5. washwashed with conc. H2SO4 (25 ml)
  6. customdried
  7. distillationdistilled in vacuo (80° C./15 mm Hg)

Sources & evidence

ORD record
ord-65842f7768b24098bcd46cc7dc77358f
Source dataset
uspto-grants-2004_07
Patent number
US06762316B1

Reaction notes

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