Dimethylformamide → 2,2-Difluoro-7-(2-m-tolyl-ethoxy)-benzo[1,3]dioxole-5-carboxylic Acid Methyl Ester

HRID 1918375Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

1.8 g of 2,2-difluoro-7-hydroxy-benzo[1,3]dioxole-5-carboxylic acid methyl ester, 4.6 g of 1-(bromo-ethyl)-3-methyl-benzene, and 3.2 g of K2CO3 were added to 70 ml of anhydrous DMF and the reaction mixture stirred at 80° C. for 3 h. The reaction mixture was then allowed to cool to room temperature, 300 ml of water added and extracted three times using 100 ml of EA each. The organic layer was then dried using MgSO4 and evaporated. Chromatography on silica gel using EA/HEP 1:4 yielded 2.4 g of the title compound, colorless oil. Rf (EA/HEP 1:4)=0.32

Workup

temperatureto cool to room temperature
extractionextracted three times
customThe organic layer was then dried
customevaporated

Sources & evidence

ORD record: ord-b75ebc47cb2644debbda52fc041be419
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618304B2

Reaction notes

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