Boron tribromide → 2-Amino-3-hydroxybenzonitrile
Reaction equation
[NH2:1][C:2]1[C:9]([O:10]C)=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].B(Br)(Br)Br>C(Cl)Cl>[NH2:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
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).
Workup
- customat room temperature
- customovernight
- customThe reaction was quenched with water
- extractionextracted with CH2Cl2
- extractionThe combined extract
- dry with materialwas dried with MgSO4
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-b8ecc2f5e83542b0ba304376338601ac
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08633186B2
Reaction notes
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