Benzyl Alcohol → HCID 86720217, compound

HRID 1754002Notes

Reaction equation

HRID 1754002 reaction equation
[NH2:1][C:2]1[C:11]([CH3:12])=[CH:10][C:9]([Br:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C[O-].[Na+].O>C1(C)C(C)=CC=CC=1>[NH2:1][C:2]1[C:11]([CH3:12])=[CH:10][C:9]([Br:13])=[CH:8][C:3]=1[C:4]([O:6][CH2:7][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:5]

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 2763413Methyl 2-amino-5-bromo-3-methylbenzoateHCID 10942334Sodium Methoxide

Product 1

HCID 86720217HCID 86720217, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of methyl 2-amino-5-bromo-3-methylbenzoate (5 g, 20.4 mmol) in benzyl alcohol (4.43 g, 40.9 mmol) and sodium methoxide (0.37 g, 2.04 mmol, 30% in methanol) was refluxed in xylene (10 ml) for 5 hours. Then, water was added, the phases were separated and the combined organic solvents were removed in vacuo. The residue was purified by column chromatography to obtain benzyl 2-amino-5-bromo-3-methylbenzoate (3.40 g, 43.3% of theory, 83.6 area % GC) as a pale brown solid.

Workup

  1. customthe phases were separated
  2. customthe combined organic solvents were removed in vacuo
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-3b66815a57c046849a9581f082bd63f2
Source dataset
uspto-grants-2015_10
Patent number
US09169198B2

Reaction notes

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