Dichloromethane → HCID 86597178, compound

HRID 130346Notes

Reaction equation

HRID 130346 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[OH:10][C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=1)[C:14]([O:16][CH3:17])=[O:15].C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>N1C=CC=CC=1.[Cu]=O>[C:5](=[C:4]1[CH:3]=[CH:2][CH:9]=[C:8]([O:10][C:11]2[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=2)[C:14]([O:16][CH3:17])=[O:15])[CH2:7]1)=[O:6]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 765833-BromobenzaldehydeHCID 88068Methyl 3-Hydroxybenzoate

Product 1

HCID 86597178HCID 86597178, compoundYield 56.1%

Reagents, catalysts & solvents 2

HCID 14829Copper oxideCatalystHCID 1049PyridineSolvent

Procedure

A mixture of 3-bromobenzaldehyde (1.000 g; 5.4 mmol), methyl 3-hydroxybenzoate (987 mg; 6.5 mmol) and potassium carbonate (1.494 g; 10.8 mmol) in dry pyridine (8 mL) is stirred under argon at RT. Copper (II) oxide (860 mg; 10.8 mmol) is added and the reaction mixture is refluxed for 12 hours. After cooling to RT, CH2Cl2 (50 mL) is added and the mixture is filtered through celite. The filter cake is washed with fresh CH2Cl2 (50 mL). The combined organics are concentrated in vacuo. The residue is purified by flash chromatography (ethyl acetate/hexanes, 1:10 to 1:4) to yield methyl 3-(3-carbonylphenoxy)benzoate (776 mg; 56%) as a yellow oil.

Workup

  1. temperaturethe reaction mixture is refluxed for 12 hours
  2. temperatureAfter cooling to RT
  3. filtrationthe mixture is filtered through celite
  4. washThe filter cake is washed with fresh CH2Cl2 (50 mL)
  5. concentrationThe combined organics are concentrated in vacuo
  6. customThe residue is purified by flash chromatography (ethyl acetate/hexanes, 1:10 to 1:4)

Sources & evidence

ORD record
ord-4861224aa9da407eb08b624b041f7ea3
Source dataset
uspto-grants-2008_06
Patent number
US07381736B2

Reaction notes

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