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Methanol → Toluene-4-sulfonic acid 4-(6-hydroxy-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinolin-1-yl)phenyl ester

HRID 397040
Notes
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Reaction equation

HRID 397040 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]([C:17]1[CH:22]=[CH:21][C:20]([O:23][S:24]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=3)(=[O:26])=[O:25])=[CH:19][CH:18]=1)[N:12]([C:34](=[O:39])[C:35]([F:38])([F:37])[F:36])[CH2:11][CH2:10]2.CO>C(Cl)Cl>[OH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]([C:17]1[CH:18]=[CH:19][C:20]([O:23][S:24]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=3)(=[O:26])=[O:25])=[CH:21][CH:22]=1)[N:12]([C:34](=[O:39])[C:35]([F:38])([F:37])[F:36])[CH2:11][CH2:10]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 86583956Toluene-4-sulfonic acid 4-(6-methoxy-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinolin-1-yl)phenyl ester

Product 1

HCID 86583957Toluene-4-sulfonic acid 4-(6-hydroxy-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinolin-1-yl)phenyl esterYield 134.6%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

Conditions

Temperature
0 °C

Procedure

A 1M solution of BBr3 in CH2Cl2 (16.2 ml, 16.2 mmol) was added slowly to a solution of toluene-4-sulfonic acid 4-(6-methoxy-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinolin-1-yl)phenyl ester (7.459 g, 14.8 mmol) in anhydrous CH2Cl2 (500 ml) at 0° C. under N2. After stirring at 0° C. for 1 hr, the reaction mixture was warmed to rt and stirred at rt for 18 hr. MeOH (250 ml) was slowly added with stirring and the resulting solution was concentrated in vacuo to give 9.793 g of brown residue. Purification by flash chromatography, eluting with hexane:EtOAc (7:3) gave 2.764 g (38% yield) of white solid.

Workup

  1. temperaturethe reaction mixture was warmed to rt
  2. stirringstirred at rt for 18 hr
  3. stirringwith stirring
  4. concentrationthe resulting solution was concentrated in vacuo

Sources & evidence

ORD record
ord-93b12d8eed2842e3b4bc59137fddba72
Source dataset
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06608203B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes