Boron tribromide → 2-(4-Acetamidophenyl)-1-(4-Hydroxybenzyl)-1,2,3,4-tetrahydroisoquinolin-6-ol

HRID 2304660Notes

Reaction equation

HRID 2304660 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:20][CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:21]C)[CH:17]=3)[CH:12]2[CH2:23][C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:20][CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([OH:21])[CH:17]=3)[CH:12]2[CH2:23][C:24]2[CH:25]=[CH:26][C:27]([OH:30])=[CH:28][CH:29]=2)=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 234407862-(4-Acetamidophenyl)-1-(4-hydroxybenzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 99522432-(4-Acetamidophenyl)-1-(4-Hydroxybenzyl)-1,2,3,4-tetrahydroisoquinolin-6-olYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(4-acetamidophenyl)-1-(4-hydroxybenzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline (0.025 g, 0.062 mmol) in 1 mL of CH2Cl2 was demethylated with BBr3 as described in Example 30.G to provide the title compound (0.018 g, 75% yield). ES-MS, (m/z) 389 [M+H]+.

Sources & evidence

ORD record
ord-c044e21334e04cc587c3420605c85a1a
Source dataset
uspto-grants-2002_08
Patent number
US06436923B1

Reaction notes

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