Benzyl Alcohol → 1-(Benzyloxy)-5-bromoisoquinoline

HRID 1403075Notes

Reaction equation

HRID 1403075 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([Br:12])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH2:13]([OH:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH-].[K+].C(=O)([O-])[O-].[K+].[K+].COCCOCCN(CCOCCOC)CCOCCOC>C1(C)C=CC=CC=1>[CH2:13]([O:20][C:2]1[C:11]2[C:6](=[C:7]([Br:12])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 5

HCID 244Benzyl AlcoholHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-HCID 211924975-Bromo-1-chloroisoquinoline

Product 1

HCID 867011321-(Benzyloxy)-5-bromoisoquinolineYield 198.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of compound (1b) (0.242 g), benzyl alcohol (0.162 g), potassium hydroxide (0.224 g), potassium carbonate (0.138 g), and tris(2-(2-methoxyethoxy)ethyl)amine (0.032 ml) in toluene (6 ml) was stirred at 120° C. for 1 hour. The reaction solution was partitioned between ethyl acetate and water. The organic layer was washed with brine and then dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was then purified by neutral silica gel column chromatography (n-hexane/ethyl acetate) to obtain compound (1c) (0.621 g, 99%) as a pale yellow solid.

Workup

  1. customThe reaction solution was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off
  5. customthe residue was then purified by neutral silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-40a16f77ac414e47a75d09bb8c4f3bbf
Source dataset
uspto-grants-2014_12
Patent number
US08912181B2

Reaction notes

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