Boron tribromide → 2-Amino-3-hydroxybenzonitrile

Temperatur

-78 °C

To a solution of 2-amino-3-methoxybenzonitrile (Example 127b) (0.98 g, 6.59 mmol) in CH2Cl2 (25.0 mL), a solution of BBr3 in CH2Cl2 (1.0M, 19.8 mL, 19.77 mmol) was added drop wise at −78° C. under a nitrogen atmosphere. The obtained mixture was stirred at −78° C. for 30 min, and then at room temperature overnight. The reaction was quenched with water, basified with saturated aqueous NaHCO3 (pH˜8) and extracted with CH2Cl2. The combined extract was dried with MgSO4, filtered and evaporated. The title compound was obtained in amount of 0.80 g (91%) as orange solid and was used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ 9.86 (broad s, 1H), 6.82-6.87 (m, 2H), 6.46 (t, J=8.0 Hz, 1H), 5.34 (broad s, 2H).

1. customat room temperature
2. customovernight
3. customThe reaction was quenched with water
4. extractionextracted with CH2Cl2
5. extractionThe combined extract
6. dry with materialwas dried with MgSO4
7. filtrationfiltered
8. customevaporated

ORD-Eintrag

ord-eb9eaf0b42034f44b5a1e009a0d0f798

Quelldatensatz

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09181276B2