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

HRID 382096

Reaction equation

HRID 382096 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-6ba6ad5d5a97434cac575961b4635e7f
Source dataset
uspto-grants-2001_10
Patent number
US06307087B1

Linked notes

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