反应详情

To a stirring solution of 4-bromo-2-chlorobenzoic acid (11.1 g, 47 mmol) in THF (100 mL) at 0° C. under nitrogen was added borane-methyl sulfide complex (9.4 ml, 94 mmol) via syringe over 10 min. Gas evolution quite evident. Ice bath removed, and once gas evolution subsided reaction gently heated to reflux for 1 h. Reaction slowly quenched with MeOH (50 mL) and 2M HCl (20 mL). Aqueous extracted with 9:1 CHCl3/IPA (150 mL). Organic dried with sat NH4Cl, MgSO4, then concentrated to a colorless oil under reduced pressure. Product crystallized after 1 week sitting neat.

1. customIce bath removed
2. customreaction
3. temperaturegently heated
4. temperatureto reflux for 1 h
5. customReaction
6. customslowly quenched with MeOH (50 mL) and 2M HCl (20 mL)
7. extractionAqueous extracted with 9:1 CHCl3/IPA (150 mL)
8. dry with materialOrganic dried with sat NH4Cl, MgSO4
9. concentrationconcentrated to a colorless oil under reduced pressure
10. customProduct crystallized after 1 week