HRID1043415

反应详情

EQUATION

反应方程式

HRID 1043415 的结构方程式

AUXILIARIES

试剂、催化剂与溶剂

2

CONDITIONS

反应条件

温度
0 °C

PROCEDURE

实验过程

4-bromobiphenyl-2-carboxylic acid (5.71 g, 20.61 mmol) was dissolved in THF (50 mL) and cooled to 0° C. 1.0M borane tetrahydrofuran complex (41.2 mL, 41.2 mmol) was added dropwise over 15 min. and allowed to warm up to r.t. overnight. The reaction was diluted with EtOAc and washed with water, sat. ammonium chloride, and then brine. The organic layer was collected, dried over MgSO4, filtered and evaporated to give the crude product. The crude product was purified by flash chromatography on the Biotage (5-35% EtOAc:Hex) to give (4-bromobiphenyl-2-yl)methanol (3.5 g, 13.30 mmol, 65% yield) as a light orange oil. LCMS: rt=1.43 min.; Phenomenex-Luna C-18 (5μ) (3.0×50 mm); Solvent A=10% acetonitrile—90% water—0.1% TFA, Solvent B=90% acetonitrile—10% water—0.1% TFA; gradient 0% to 100% solvent B over 2 min. and then hold for 1 min.; 4 mL/min; inj. vol.=5 uL; wavelength=220. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 4.60 (d, J=5.77 Hz, 2H) 7.15 (d, J=8.28 Hz, 1H) 7.29-7.35 (m, 2H) 7.36-7.46 (m, 3H) 7.48 (dd, J=8.28, 2.01 Hz, 1H) 7.75 (d, J=2.01 Hz, 1H).

WORKUP

后处理

  1. addition1.0M borane tetrahydrofuran complex (41.2 mL, 41.2 mmol) was added dropwise over 15 min.
  2. temperatureto warm up to r.t. overnight
  3. washwashed with water, sat. ammonium chloride
  4. customThe organic layer was collected
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customto give the crude product
  9. customThe crude product was purified by flash chromatography on the Biotage (5-35% EtOAc:Hex)