Chlorodicyclohexylphosphine → 2-(Dicyclohexylphosphino)-2'-methoxybiphenyl

HRID 496930

Reaction equation

HRID 496930 reaction equation
CC1C=[CH:6][C:5]([CH:8]([C:14]2[CH:19]=[CH:18][C:17](C)=[CH:16][CH:15]=2)[C:9](=[O:13])[CH:10]([CH3:12])C)=CC=1.[Li][CH2:22]CCC.Cl[P:27]([CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1)[CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1>C1COCC1>[CH:28]1([P:27]([CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]2)[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:8]2[CH:5]=[CH:6][CH:12]=[CH:10][C:9]=2[O:13][CH3:22])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 2734135ChlorodicyclohexylphosphineHCID 120407443-Methyl-1,1-bis(4-methylphenyl)-2-butanoneHCID 178418339Butyllithium

Product 1

HCID 117941862-(Dicyclohexylphosphino)-2'-methoxybiphenylYield 54.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1 (535 mg, 2.03 mmol) in THF (20 mL) was cooled to −78° C. under argon, then n-BuLi (1.6 M in hexane, 1.35 mL, 2.16 mmol) was added dropwise. After 2.5 h at −78° C., a solution of chlorodicyclohexylphosphine (570 mg, 2.45 mmol) in THF (3 mL) was added over 10 min. The reaction mixture was then allowed to warm to room temperature overnight, then quenched with saturated aqueous NaHCO3 and concentrated in vacuo. The resulting aqueous suspension was extracted with ether (2×50 mL), and the combined ethereal layers were dried (Na2SO4), filtered and concentrated in vacuo. The resulting crude solid was recrystallized from ethanol to afford 420 mg (54%) of a white solid.

Workup

  1. customquenched with saturated aqueous NaHCO3
  2. concentrationconcentrated in vacuo
  3. extractionThe resulting aqueous suspension was extracted with ether (2×50 mL)
  4. dry with materialthe combined ethereal layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting crude solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-2aac3abf10d6404c9f7ff39698b50a7e
Source dataset
uspto-grants-2005_09
Patent number
US06946560B2

Linked notes

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