Benzophenone → diphenyl-(2-phenylphenyl)methanol

HRID 2374109Notes

Reaction equation

HRID 2374109 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Li]CCCC.[C:19]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1>[C:27]1([C:19]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([C:2]2[C:3]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[CH:4][CH:5]=[CH:6][CH:7]=2)[OH:26])[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 3102BenzophenoneHCID 163292-BromobiphenylHCID 178418339Butyllithium

Product 1

HCID 410659diphenyl-(2-phenylphenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

α,α-Diphenyl-2-biphenylmethanol was prepared by the following procedure (Reaction Scheme 1). To a solution of 2-bromobiphenyl (5.00 g, 21.45 mmol) in freshly distilled THF (50 mL) at −78° C. was added n-BuLi (1.37 g, 21.45 mmol, 8.6 mL of 2.5 M solution in hexanes) dropwise via syringe. Approximately 5 minutes after complete addition, benzophenone (4.10 g, 22.52 mmol) was added in a single portion, after which time the ice bath was removed and the solution allowed to warm to room temperature. After 2 h, the reaction was quenched with the addition of NH4Cl and H2O (100 mL), and extracted with Et2O (3×100 mL). The combined organic layers were washed with brine, dried over MgSO4, and concentrated to dryness. Chromatography gave the product as a white solid (6.27 g, 87% yield).

Workup

  1. additionwas added in a single portion
  2. customafter which time the ice bath was removed
  3. customthe reaction was quenched with the addition of NH4Cl and H2O (100 mL)
  4. extractionextracted with Et2O (3×100 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-2ce7cecdadc443838848401fb13f1e3b
Source dataset
uspto-grants-2008_12
Patent number
US07462405B2

Reaction notes

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