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

HRID 625033Notes

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 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. The reaction mixture was then warmed to room temperature and stirred for 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
temperatureThe reaction mixture was then warmed to room temperature
stirringstirred for 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-5f323eb7e8bb42e38844d5a64227a618
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09303040B2

Reaction notes

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