Boron tribromide → HCID 86719509, compound
Reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([NH2:17])=[C:10]2[C:13]([F:16])([F:15])[F:14])=[CH:5][CH:4]=1.B(Br)(Br)Br>ClCCl>[NH2:17][C:9]1[C:10]([C:13]([F:14])([F:15])[F:16])=[C:11]2[C:6]([CH:5]=[CH:4][C:3]([OH:2])=[CH:12]2)=[CH:7][CH:8]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of 7-methoxy-1-(trifluoromethyl)naphthalen-2-amine (2 g, 8.29 mmol) in dichloromethane (20 ml) was added dropwise BBr3 (4 ml, 42 mmol, 5 eq.) with stirring at −78° C. The resulting solution was stirred overnight at room temperature and then quenched by ice—water (50 ml) and extracted with dichloromethane (3×50 ml). The combined organic layers were dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum to afford 7-amino-8-(trifluoromethyl)naphthalen-2-ol as a brown solid (1.3 g, 69%).
Workup
- stirringThe resulting solution was stirred overnight at room temperature
- customquenched by ice—water (50 ml)
- extractionextracted with dichloromethane (3×50 ml)
- dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-58886016d3434319b749ecdc7c8d6527
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09249102B2
Reaction notes
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