Sodium borohydride → HCID 61099758, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:19])=[C:6]([C:8]([C:10]2[CH:11]=[CH:12][C:13]3[O:17][CH2:16][CH2:15][C:14]=3[CH:18]=2)=[O:9])[CH:7]=1.[BH4-].[Na+]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:19])=[C:6]([CH:8]([C:10]2[CH:11]=[CH:12][C:13]3[O:17][CH2:16][CH2:15][C:14]=3[CH:18]=2)[OH:9])[CH:7]=1Participants
3
Conditions
- Temperature
- 0 °C
Procedure
(5-bromo-2-chloro-phenyl)-(2,3-dihydrobenzofuran-5-yl)methanone 5b (10.47 g, 31.0 mmol) was dissolved in 100 mL of mixed solution (THF and MeOH, v:v=1:1) and cooled to 0° C., followed by addition of sodium borohydride (2.35 g, 62.0 mmol) in batch. The reaction mixture was stirred for 30 minutes at 0° C. Thereafter, the reaction mixture was concentrated under reduced pressure after 20 mL acetone were added. The resulting residue was dissolved in 250 mL ethyl acetate and partitioned. The organic extract was washed with water (100 mL×2), combined, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound (5-bromo-2-chloro-phenyl)-(2,3-dihydrobenzofuran-5-yl)methanol 5c (10.5 g, pale yellow grease), yield: 99.7%. 1H NMR (400 MHz, CDCl3): δ 7.88 (d, 1H), 7.34 (dd, 1H), 7.18 (d, 1H), 7.16 (s, 1H), 7.11 (dd, 1H), 6.73 (d, 1H), 6.05 (s, 1H), 4.56 (t, 2H), 3.18 (t, 2H), 2.27 (s, 1H).