Toluene → Bis(adamantan-1-yl)(butyl)phosphane

HRID 857835Notes

Reaction equation

HRID 857835 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][CH2:23][CH2:24][CH2:25][CH3:26].C1(C)C=CC=CC=1.C(Br)CCC>C(OCCCC)CCC>[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)[CH2:23][CH2:24][CH2:25][CH3:26])[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 4

HCID 1140TolueneHCID 8002Butyl bromideHCID 11077518Di-1-adamantylphosphineHCID 178418339Butyllithium

Product 1

HCID 11371790Bis(adamantan-1-yl)(butyl)phosphane

Reagents, catalysts & solvents 1

HCID 8909Butyl etherSolvent

Procedure

4.6 g (15 mmol) of di(1-adamantyl)phosphine were placed in 50 ml of di-n-butyl ether, and 20 ml of a 2.5 M solution of n-BuLi in toluene (50 mmol) were added. The mixture was refluxed for 1 h and cooled and 4.1 g (30 mmol) of 1-butyl bromide 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 1 h
  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-5940c09a5928463c9261bc1c3cda896e
Source dataset
uspto-grants-2006_12
Patent number
US07148176B2

Reaction notes

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