Boron tribromide → 3-(4-Chloro-benzylamino)-phenol
Reaction equation
B(Br)(Br)Br.[Cl:5][C:6]1[CH:21]=[CH:20][C:9]([CH2:10][NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18]C)[CH:13]=2)=[CH:8][CH:7]=1>ClCCl>[Cl:5][C:6]1[CH:21]=[CH:20][C:9]([CH2:10][NH:11][C:12]2[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=2)=[CH:8][CH:7]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Boron tribromide (2.59 ml, 27.4 mmol) was added drop wise to a cool stirred solution of (4-chloro-benzyl)-(3-methoxy-phenyl)-amine (2.37 g, 9.6 mmol) in anhydrous dichloromethane (90 ml) and the mixture was stirred at 0° C. for 1 hour then ambient for 15 hours. The reaction was cooled to 0° C. and quenched with the addition of saturated sodium bicarbonate solution (aq) (100 ml). The aqueous layer was collected and extracted further with dichloromethane (2×100 ml) and combined organic extracts were concentrated in vacuo to obtain crude product. The crude residue was purified by flash chromatography (SiO2) eluting with 5% ethyl acetate/dichloromethane to yield a cream solid (1.58 g, 71% yield). HPLC retention time 4.55 min Mass spectrum (ES+) m/z 234 (M+H).
Workup
- waitambient for 15 hours
- temperatureThe reaction was cooled to 0° C.
- customquenched with the addition of saturated sodium bicarbonate solution (aq) (100 ml)
- customThe aqueous layer was collected
- extractionextracted further with dichloromethane (2×100 ml)
- concentrationwere concentrated in vacuo
- customto obtain crude product
- customThe crude residue was purified by flash chromatography (SiO2)
- washeluting with 5% ethyl acetate/dichloromethane
Sources & evidence
- ORD record
- ord-261b15abf91f4c769b7dd6227a453246
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08372840B2
Reaction notes
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