Water → (Z)-methyl 2-(tert-butoxycarbonyl)-3-(4-chloro-3-fluorophenyl)acrylate

HRID 532725Notes

Reaction equation

CN(C)C(N(C)C)=N.[C:9]([O:13][C:14]([CH:16](P(OC)(OC)=O)[C:17]([O:19][CH3:20])=[O:18])=[O:15])([CH3:12])([CH3:11])[CH3:10].[Cl:27][C:28]1[CH:35]=[CH:34][C:31]([CH:32]=O)=[CH:30][C:29]=1[F:36].O>C(Cl)Cl>[C:9]([O:13][C:14](/[C:16](=[CH:32]\[C:31]1[CH:34]=[CH:35][C:28]([Cl:27])=[C:29]([F:36])[CH:30]=1)/[C:17]([O:19][CH3:20])=[O:18])=[O:15])([CH3:10])([CH3:11])[CH3:12]

Participants

Conditions

Temperature: 0 °C

Procedure

1,1,3,3-Tetramethylguanidine (2.11 ml, 16.8 mmol) was added to a 0° C. solution of methyl 2-(tert-butoxycarbonyl)-2-(dimethoxyphosphoryl)-acetate (5.00 g, 16.8 mmol) in DCM (70 mL). The reaction mixture was stirred at 0° C. for 30 minutes. Then a solution of 4-chloro-3-fluorobenzaldehyde (2.67 g, 16.8 mmol) in DCM (10 mL) was added by syringe. The reaction mixture was stirred for 10 minutes, then warmed to room temperature and stirred for another 1 hour. H2O was then added, and the mixture was extracted with DCM. The combined extracts were dried (Na2SO4), filtered, and concentrated. The resulting solids were recrystallized from IPA to give (Z)-methyl 2-(tert-butoxycarbonyl)-3-(4-chloro-3-fluorophenyl)acrylate (3.76 g, 67.8% yield) as a white powder (2 crops). LCMS (APCI−) m/z 328 [M−H]−.

Workup

stirringThe reaction mixture was stirred for 10 minutes
temperaturewarmed to room temperature
stirringstirred for another 1 hour
extractionthe mixture was extracted with DCM
dry with materialThe combined extracts were dried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customThe resulting solids were recrystallized from IPA

Sources & evidence

ORD record: ord-30ebf75709f443d0bfb2518cd29498f0
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853199B2

Reaction notes

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