Sodium Carbonate → 3-[(1E)-3-Methoxyprop-1-en-1-yl]-5-(trifluoromethyl)benzaldehyde

HRID 337642Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)[CH:5]=[O:6].CC1(C)C(C)(C)OB(/[CH:22]=[CH:23]/[CH2:24][O:25][CH3:26])O1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.O>[CH3:26][O:25][CH2:24]/[CH:23]=[CH:22]/[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)[CH:5]=[O:6]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 3-bromo-5-(trifluoromethyl)benzaldehyde (1 eq.) from the previous step and 4,4,5,5-tetramethyl-2-[(1E)-3-(methyloxy)-1-propen-1-yl]-1,3,2-dioxaborolane (1.5 eq.) in DMF (0.2 M) was added trans-bis(triphenylphosphine) palladium(II) bromide (0.05 eq.). The vessel was repeatedly evacuated and back-filled with nitrogen. Finally, 2 M aq. Na2CO3 (3 eq.) was added and the resulting mixture was stirred at 100° C. for 2 h. The now black suspension was cooled to RT, diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with water and brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product by way of flash chromatography (SiO2, 9:1 (v/v) Hex:EtOAc→EtOAc) afforded the title compound as a yellow oil.

Workup

customThe vessel was repeatedly evacuated
additionback-filled with nitrogen
temperatureThe now black suspension was cooled to RT
extractionextracted with ethyl acetate
washThe combined organic extracts were washed with water and brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationthe filtrate concentrated in vacuo
customPurification of the crude product by way of flash chromatography (SiO2, 9:1 (v/v) Hex:EtOAc→EtOAc)

Sources & evidence

ORD record: ord-0deea1571f2b42fa8d38994ed1b96afd
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889714B2

Reaction notes

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