Benzyl Alcohol → 6-(Benzyloxy)-8-bromoisoquinoline

HRID 2069083Notes

Reaction equation

HRID 2069083 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN(C(/N=N/C(N(C)C)=O)=O)C.[Br:40][C:41]1[CH:42]=[C:43](O)[CH:44]=[C:45]2[C:50]=1[CH:49]=[N:48][CH:47]=[CH:46]2>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:43]1[CH:44]=[C:45]2[C:50](=[C:41]([Br:40])[CH:42]=1)[CH:49]=[N:48][CH:47]=[CH:46]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 11776TriphenylphosphineHCID 5353800DiamideHCID 1357421998-Bromoisoquinolin-6-ol

Product 1

HCID 674026996-(Benzyloxy)-8-bromoisoquinoline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Benzyl alcohol (0.25 mL; Ald), triphenylphosphine (1.29 g), and TMAD (850 mg; Ald) were added to a toluene (30 mL) solution of Intermediate 7 (500 mg) and the resulting mixture was stirred at room temperature for 13 hours. The reaction mixture solution was filtrated, the solvent was evaporated under reduced pressure, and the residue was purified by column chromatography (Yamazen; n-hexane/ethyl acetate) to give the title compound (186 mg).

Workup

  1. filtrationThe reaction mixture solution was filtrated
  2. customthe solvent was evaporated under reduced pressure
  3. customthe residue was purified by column chromatography (Yamazen; n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-1873497c12c84a3685fd0a06d7ac0774
Source dataset
uspto-grants-2012_10
Patent number
US08299055B2

Reaction notes

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