Potassium Carbonate → Ethyl 2-(3-bromo-5-chloro-4-(cyclopropylmethoxy)phenyl)acetate

HRID 1183741Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[C:6]([Cl:9])[C:7]=1[OH:8].C([O-])([O-])=O.[K+].[K+].[CH:22]1([CH2:25]Br)[CH2:24][CH2:23]1>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[C:6]([Cl:9])[C:7]=1[O:8][CH2:25][CH:22]1[CH2:24][CH2:23]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of ethyl 2-(3-bromo-5-chloro-4-hydroxyphenyl)acetate (12 g, 40.816 mmol) in DMSO (80 mL) were added K2CO3 (14.08 g, 102.020 mmol) and cyclopropylmethylbromide (5 mL, 4.880 mmol) at RT under inert atmosphere. The reaction mixture was stirred at 80° C. temperature over a period of 14 h. After completion of starting material (by TLC), the reaction mixture was cooled to RT and quenched with water and extracted with EtOAc (3×100 mL). Combined organic layers were washed with water (3×75 mL), brine and dried over Na2SO4. After filtration and concentration under reduced pressure, the crude material was purified by column chromatography to afford ethyl 2-(3-bromo-5-chloro-4-(cyclopropylmethoxy)phenyl)acetate (10 g) yellow solid.

Workup

temperatureAfter completion of starting material (by TLC), the reaction mixture was cooled to RT
customquenched with water
extractionextracted with EtOAc (3×100 mL)
washCombined organic layers were washed with water (3×75 mL), brine
dry with materialdried over Na2SO4
filtrationAfter filtration and concentration under reduced pressure
customthe crude material was purified by column chromatography

Sources & evidence

ORD record: ord-27050f6749ac4cc9930d5b59defa56d6
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08664249B2

Reaction notes

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