Phosphorus tribromide → 1-Bromo-11-methoxy-3,7,11-trimethyldodeca-2,4-diene

HRID 918334Notes

Reaction equation

HRID 918334 reaction equation
[CH3:1][O:2][C:3]([CH3:18])([CH3:17])[CH2:4][CH2:5][CH2:6][CH:7]([CH3:16])[CH2:8][CH:9]=[CH:10][C:11]([CH3:15])=[CH:12][CH2:13]O.P(Br)(Br)[Br:20]>CCOCC>[CH3:1][O:2][C:3]([CH3:18])([CH3:17])[CH2:4][CH2:5][CH2:6][CH:7]([CH3:16])[CH2:8][CH:9]=[CH:10][C:11]([CH3:15])=[CH:12][CH2:13][Br:20]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 5428054911-Methoxy-3,7,11-trimethyldodeca-2,4-dien-1-ol

Product 1

HCID 538762881-Bromo-11-methoxy-3,7,11-trimethyldodeca-2,4-diene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 1.90 g. of 11-methoxy-3,7,11-trimethyldodeca-2,4-dien-1-ol in 20 ml. of ether is added a solution of 0.80 g. of phosphorus tribromide in 10 ml. of ether, under nitrogen, with stirring at -50°. The reaction mixture is stirred for three hours at -60° to -40° and then poured into ice water, which is then washed with sodium bicarbonate solution water and brine, dried over calcium sulfate and evaporated under reduced pressure to yield 11-methoxy-3,7,11-trimethyldodeca-2,4-dienyl bromide.

Workup

  1. washis then washed with sodium bicarbonate solution water and brine
  2. dry with materialdried over calcium sulfate
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-be9f73a0529b48b9b6f8552633cee6f0
Source dataset
uspto-grants-1976_07
Patent number
US03970704

Reaction notes

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