Ammonium Chloride → (2-(Benzyloxy)-3-tert-butylphenyl)(2'-methoxybiphenyl-3-yl)(phenyl)methanol

HRID 45466Notes

Reaction equation

HRID 45466 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][CH3:15])[CH:5]=[CH:6][CH:7]=1.C([Li])CCC.[CH2:21]([O:28][C:29]1[C:34]([C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:33][CH:32]=[CH:31][C:30]=1[C:39]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:40])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:21]([O:28][C:29]1[C:34]([C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:33][CH:32]=[CH:31][C:30]=1[C:39]([C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][CH3:15])[CH:5]=[CH:6][CH:7]=1)([C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[OH:40])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 186686213'-Bromo-2-methoxybiphenylHCID 58238504(2-(Benzyloxy)-3-tert-butylphenyl)(phenyl)methanoneHCID 178418339Butyllithium

Product 1

HCID 58238592(2-(Benzyloxy)-3-tert-butylphenyl)(2'-methoxybiphenyl-3-yl)(phenyl)methanolYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3′-bromo-2-methoxybiphenyl (1 g, 3.8 mmol) in anhydrous tetrahydrofuran (15 mL) was stirred at −78° C. and 2.5M n-butyllithium in hexanes (1.6 mL, 4 mmol) was added at such a rate that the temperature did not exceed −70° C. Stirring was continued at −78° C. for 1 hr. A solution of (2-(benzyloxy)-3-tert-butylphenyl)(phenyl)methanone (1.3 g, 3.8 mmol) in tetrahydrofuran (5 mL) was added at such a rate that the temperature did not exceed −65° C. The reaction mixture was allowed to reach room temperature slowly and was poured onto saturated ammonium chloride (100 mL) and extracted with ethyl acetate (150 mL). The organic extract was washed with water (2×80 mL). The organic layer was dried over sodium sulfate, filtered and the solvent was removed on a rotary evaporator. The crude product was purified by chromatography on silica (80 g) with 2% ethyl acetate in heptane (3.5 L). Pure 29 (1.2 g, 60%) was isolated.

Workup

  1. customdid not exceed −70° C
  2. customdid not exceed −65° C
  3. customto reach room temperature
  4. extractionextracted with ethyl acetate (150 mL)
  5. extractionThe organic extract
  6. washwas washed with water (2×80 mL)
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. filtrationfiltered
  9. customthe solvent was removed on a rotary evaporator
  10. customThe crude product was purified by chromatography on silica (80 g) with 2% ethyl acetate in heptane (3.5 L)

Sources & evidence

ORD record
ord-7143236d711a4fbeb76e6c15d3763690
Source dataset
uspto-grants-2013_09
Patent number
US08541522B2

Reaction notes

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