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

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.

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)

ORD record

ord-7143236d711a4fbeb76e6c15d3763690

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08541522B2