Triethylamine → Methyl 3-phenoxy-2-hydroxybenzoate

HRID 750456Notes

Reaction equation

HRID 750456 reaction equation
[OH:1][C:2]1[C:11]([OH:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[O:12]([C:11]1[C:2]([OH:1])=[C:3]([CH:8]=[CH:9][CH:10]=1)[C:4]([O:6][CH3:7])=[O:5])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 75484Methyl 2,3-Dihydroxybenzoate

Product 1

HCID 22263553Methyl 3-phenoxy-2-hydroxybenzoateYield 11.5%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of methyl 2,3-dihydroxybenzoate (1.50 g, 8.9 mmol), phenylboronic acid (1.08 g, 8.9 mmol) and copper acetate (1.62 g, 8.9 mmol) suspended in dichloromethane (100 ml) was added triethylamine (6.15 ml, 44.5 mmol) and the mixture was stirred at room temperature for 96 h. The solvent was removed and the product chromatographed through a silica column using a gradient of 0-10% methanol in dichloromethane. The product was obtained as a pale yellow oil (0.25 g).

Workup

  1. customThe solvent was removed
  2. customthe product chromatographed through a silica column

Sources & evidence

ORD record
ord-7ea1d1deedba458f9734af2f5e0cbd22
Source dataset
uspto-grants-2008_07
Patent number
US07405211B2

Reaction notes

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