Phosphorus tribromide → 4-(Bromomethyl)heptane
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
- temperatureto maintain the temperature below 0° C.
- temperatureThe reaction mixture was heated at 100° C. for 1 h
- temperaturecooled to room temperature
- customThe organic layer was separated
- washwashed with conc. H2SO4 (25 ml)
- customdried
- 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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