Sodium hydride → Ethyl 2-(3-bromo-5-chloro-4-(2,2,2-trifluoroethoxy)phenyl)-3-cyclopropylpropanoate

HRID 385445Notes

Reaction equation

[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:7]=[C:8]([Cl:16])[C:9]=1[O:10][CH2:11][C:12]([F:15])([F:14])[F:13].[CH:23]1([CH2:26]Br)[CH2:25][CH2:24]1>CN(C=O)C>[Br:3][C:4]1[CH:5]=[C:6]([CH:17]([CH2:26][CH:23]2[CH2:25][CH2:24]2)[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:7]=[C:8]([Cl:16])[C:9]=1[O:10][CH2:11][C:12]([F:15])([F:13])[F:14]

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of NaH (0.327 g, 60% in paraffin oil, 8.1 mmol) in DMF (100 mL), slowly added a mixture of ethyl 2-(3-bromo-5-chloro-4-(2,2,2-trifluoroethoxy)phenyl)acetate (3.0 g, 6.8 mmol) and cyclopropyl methylbromide (0.718 mL, 7.5 mmol) dissolved in DMF (20 mL) at 0° C. for 15 min under an atmosphere of nitrogen. The reaction mixture was allowed stir at 0° C. for 15 min, upon which the mixture was poured onto crushed ice and extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with water, brine, dried over Na2SO4 and evaporated. The residue was purified by Flash column chromatography to give compound ethyl 2-(3-bromo-5-chloro-4-(2,2,2-trifluoroethoxy)phenyl)-3-cyclopropylpropanoate (2.35 g) as a thick syrup.

Workup

additionslowly added
additionwas poured
customonto crushed ice
extractionextracted with ethyl acetate (2×50 mL)
washThe combined organic layers were washed with water, brine
dry with materialdried over Na2SO4
customevaporated
customThe residue was purified by Flash column chromatography

Sources & evidence

ORD record: ord-d237c2f027a54d3a9ffbbf6ad5a51bf0
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367863B2

Reaction notes

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