Water → Methyl 5-chloro-2-[(2-chlorophenoxy)methyl]benzoate

HRID 493518Notes

Reaction equation

BrC[CH2:3][C:4]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7].[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[OH:22].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:14][C:11]1[CH:12]=[CH:13][C:4]([CH2:3][O:22][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[Cl:15])=[C:5]([CH:10]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of methyl 2-(bromoethyl)-5-chlorobenzoate (100 mg, 0.38 mmol), 2-chlorophenol (43 μL, 0.42 mmol) and potassium carbonate (105 mg, 0.76 mmol) in N,N-dimethylforamide (2 mL) was stirred at room temperature for 3 h and at 50° C. for 4 hours. Water (5 mL) was added and the mixture was extracted with diethyl ether (15 mL×2). The combined organic extracts were washed with brine (15 mL) and dried (sodium sulfate). After removal of solvent, the residue was purified by pTLC eluting with hexane/ethyl acetate (9/1) to afford 103 mg (87%) of the title compound:

Workup

extractionthe mixture was extracted with diethyl ether (15 mL×2)
washThe combined organic extracts were washed with brine (15 mL)
dry with materialdried (sodium sulfate)
customAfter removal of solvent
customthe residue was purified by pTLC
washeluting with hexane/ethyl acetate (9/1)

Sources & evidence

ORD record: ord-fe33ae33831048b8a41e7ef4f08f6e62
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07534914B2

Reaction notes

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