1-Bromohexane → Hexyldiadamantyl-phosphine

HRID 857836Notes

Reaction equation

HRID 857836 reaction equation
[C:1]12([PH:11][C:12]34[CH2:21][CH:16]5[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]5)[CH2:13]3)[CH2:19]4)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[Li]CCCC.Br[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]>C(OCCCC)CCC.C1(C)C=CC=CC=1>[C:1]12([P:11]([C:12]34[CH2:19][CH:18]5[CH2:20][CH:14]([CH2:15][CH:16]([CH2:17]5)[CH2:21]3)[CH2:13]4)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:2][CH:3]3[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]3)[CH2:10]1)[CH2:8]2

Participants

6

Reactant 3

HCID 81011-BromohexaneHCID 11077518Di-1-adamantylphosphineHCID 178418339Butyllithium

Product 1

HCID 58194762Hexyldiadamantyl-phosphine

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8909Butyl etherSolvent

Procedure

5.5 g (18 mmol) of di(1-adamantyl)phosphine were placed in 60 ml of di-n-butyl ether, and 20 ml of a 2.5 M solution of n-BuLi (50 mmol) in toluene were added. The mixture was refluxed for 45 min and cooled and 3.0 g (18 mmol) of 1-bromohexane were added dropwise. The mixture was refluxed for 30 min, cooled and washed with saturated ammonium chloride solution (3×), the organic phase was separated off and dried over sodium sulfate and the solvent was distilled off under reduced pressure.

Workup

  1. temperatureThe mixture was refluxed for 45 min
  2. temperaturecooled
  3. temperatureThe mixture was refluxed for 30 min
  4. temperaturecooled
  5. washwashed with saturated ammonium chloride solution (3×)
  6. customthe organic phase was separated off
  7. dry with materialdried over sodium sulfate
  8. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-90ba997d21cb43acbe932573ca768450
Source dataset
uspto-grants-2006_12
Patent number
US07148176B2

Reaction notes

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