Boron tribromide → 7-Amino-8-benzyl-5,6,7,8-tetrahydronaphthalen-2-ol
Reaction equation
[CH2:1]([CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18]C)[CH:16]=2)[CH2:11][CH2:10][CH:9]1[NH2:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br>ClCCl>[NH2:20][CH:9]1[CH:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:17]2[CH:16]=[C:15]([OH:18])[CH:14]=[CH:13][C:12]=2[CH2:11][CH2:10]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 1-benzyl-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-amine (2.56 g, 9.57 mmol) in dry dichloromethane (47.4 mL) under Argon at 0° C. 1M BBr3 in dichloromethane (23.93 mL, 23.93 mmol) was added. The cooling bath was removed and the reaction was allowed to reach room temperature overnight. The reaction was quenched with water, and 1 M NaOH was added to alkalinity. The organic layer was separated and the aqueous phase was extracted with dichloromethane (4×50 mL). The collected organic extracts were concentrated until the product precipitated as a green solid. The solid was collected via filtration and washed with cold dichloromethane (ca. 10 mL). The solid obtained was dried to a gray-greenish powder (2.233 g, 8.81 mmol, 92%).