Hydrogen Bromide → 1-(4-Bromo-phenyl)-3,4-dihydro-isoquinolin-6-ol

HRID 342214Notes

Reaction equation

HRID 342214 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:18]C)=[CH:15][CH:16]=3)[CH2:11][CH2:10][N:9]=2)=[CH:4][CH:3]=1.Br>C(O)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([OH:18])=[CH:15][CH:16]=3)[CH2:11][CH2:10][N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 118232271-(4-Bromo-phenyl)-6-methoxy-3,4-dihydro-isoquinoline

Product 1

HCID 1359807951-(4-Bromo-phenyl)-3,4-dihydro-isoquinolin-6-olYield 95.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Cleavage of the methoxy protecting group (analogously to Ex. 14c) from 1-(4-bromo-phenyl)-6-methoxy-3,4-dihydro-isoquinoline (15 g) is effected with 95 ml of acetic acid and 65 ml of 62% aqueous hydrobromide solution at 100° C. and gives 13.7 g of 1-(4-bromo-phenyl)-3,4-dihydro-isoquinolin-6-ol, MS: m/e 301 (M+, 1 Br).

Sources & evidence

ORD record
ord-ac9ed99a7ec249568ce12d15d37cefee
Source dataset
uspto-grants-1999_01
Patent number
US05856503

Reaction notes

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