Boron tribromide → 2-Amino-3-hydroxybenzonitrile

온도

-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 기록

ord-b8ecc2f5e83542b0ba304376338601ac

출처 데이터셋

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08633186B2