Triphenylphosphine → (3R,7R)-1-bromo-3,7,11-trimethyldodecane

HRID 1390188Notes

Reaction equation

HRID 1390188 reaction equation
[CH3:1][C@H:2]([CH2:6][CH2:7][CH2:8][C@H:9]([CH3:16])[CH2:10][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[CH2:3][CH2:4]O.[Br:17]N1C(=O)CCC1=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:17][CH2:4][CH2:3][C@H:2]([CH3:1])[CH2:6][CH2:7][CH2:8][C@H:9]([CH3:16])[CH2:10][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 1590641-Dodecanol, 3,7,11-trimethyl-, (R*,R*)-

Product 1

HCID 13191851(3R,7R)-1-bromo-3,7,11-trimethyldodecaneYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.1 g (13.6 mmol) of (3R,7R)-3,7,11-trimethyl-1-dodecanol are treated with 4.02 g (15.3 mmol) of N-bromosuccinimide and 2.62 g (14.7 mmol) of triphenylphosphine in 13 ml of methylene chloride according to the method described above in Example 10. After chromatography and distillation, there are obtained 3.54 g (90%) of (3R,7R)-bromo-3,7,11-trimethyldodecane. B.p. 90°/0.05 Torr; [α]D20 = -3.6 (c = 1.005, n-octane).

Workup

  1. distillationAfter chromatography and distillation, there

Sources & evidence

ORD record
ord-3a46ead1aa0a4b02a201aff18ed2b396
Source dataset
uspto-grants-1979_02
Patent number
US04138289

Reaction notes

Loading…