Dichloromethane → Methyl 5-bromo-2-(2-(4-chlorophenoxy)acetamido)benzoate

HRID 520843Notes

Reaction equation

[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Cl:13][C:14]1[CH:24]=[CH:23][C:17]([O:18][CH2:19][C:20](Cl)=[O:21])=[CH:16][CH:15]=1.ClCCl.C(N(CC)CC)C>C1COCC1>[Br:12][C:9]1[CH:10]=[CH:11][C:2]([NH:1][C:20](=[O:21])[CH2:19][O:18][C:17]2[CH:23]=[CH:24][C:14]([Cl:13])=[CH:15][CH:16]=2)=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of methyl 2-amino-5-bromobenzoate (3.03 mL, 17.4 mmol) in THF (28 mL) was added 2-(4-chlorophenoxy)acetyl chloride (3.92 g, 19.1 mmol) to form a suspension. An additional 30 mL of dichloromethane was added. The reaction was then cooled to 0° C. and triethylamine (5.32 mL, 38.3 mmol) was added dropwise. The cold bath was removed and the reaction was stirred at room temperature for 2 hours. Analysis showed the reaction to be incomplete, so additional 2-(4-chlorophenoxy)acetyl chloride (0.5 mL, 3.22 mmol) was added and reaction solution was stirred for 1 hour then transferred to a reparatory funnel with dichloromethane dilution. The organic phase was washed with water and saturated aqueous NH4Cl solution, then dried (MgSO4), filtered, and concentrated to yield the title compound.

Workup

customto form a suspension
customThe cold bath was removed
customthe reaction
customreaction solution
stirringwas stirred for 1 hour
washThe organic phase was washed with water and saturated aqueous NH4Cl solution
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-adedb6c4eacf408c8b627767fef1ce96
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328095B2

Reaction notes

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