HRID332892

反应详情

EQUATION

反应方程式

HRID 332892 的结构方程式

AUXILIARIES

试剂、催化剂与溶剂

1

CONDITIONS

反应条件

温度
0 °C

PROCEDURE

实验过程

To a 2-dram vial containing (E)-tert-butyl 3-(4-((6-methoxy-2-(4-(trifluoromethyl)phenyl)benzo[b]thiophen-3 yl)oxy)phenyl)acrylate (59.4 mg, 0.113 mmol) in anhydrous DCM (1.5 mL) at 0° C. was added BBr3 (1.0 M in DCM, 451 μL, 0.451 mmol) dropwise. The resulting mixture was stirred at 0° C. for 1 h after which the reaction was quenched with 3 drops of water, diluted with DCM, and extracted with sat. aq. NaHCO3 (added a few drops of 2-propanol). The organic layer was dried over anhydrous MgSO4, filtered concentrated in vacuo to afford the crude material which was purified by reverse phase HPLC (neutral condition, 3% 1-propanol in 10-100% CH3CN/H2O) to afford (E)-3-(4-((6-hydroxy-2-(4-(trifluoromethyl)phenyl)benzo[b]thiophen-3-yl)oxy)phenyl)acrylic acid (33.8 mg, 0.074 mmol, 66% yield) as a white solid. 1H NMR (400 MHz, CD3OD) δ ppm=6.36 (d, J=16.17 Hz, 1H), 6.78-6.89 (m, 1H), 6.98 (d, J=8.59 Hz, 2H), 7.17-7.30 (m, 2H), 7.51-7.70 (m, 5H), 7.88 (d, J=8.08 Hz, 2H). HRMS (m/z, MH+): 457.0710.

WORKUP

后处理

  1. customwas quenched with 3 drops of water
  2. additiondiluted with DCM
  3. extractionextracted with sat. aq. NaHCO3 (added a few drops of 2-propanol)
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford the crude material which
  8. customwas purified by reverse phase HPLC (neutral condition, 3% 1-propanol in 10-100% CH3CN/H2O)