Water → 1-(2,4-Difluorophenyl)-2-(3,5-d-imethoxy-4-1-propylphenyl)ethene

HRID 252331Notes

Reaction equation

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

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of (3,5-dimethoxy-4-1-propylphenyl)ethene (0.649 g, 3.15 mmol), 1-bromo-2,4-difluorobenzene (1.23 g, 6.37 mmol), dihydrogen di-μ-chlorotetrkis(di-tert-butylphosphinito-KP)dipalladate (0.1409 g, 0.151 mmol), Bu4NI (0.582 g, 1.58 mmol) and K2CO3 (1.45 g, 10.5 mmol) in DMF (10 mL) was heated at 140° C. under argon. After the reaction was complete (6 h), the reaction mixture was poured into water (10 ml). The aqueous was acidified with 2NHCl and extracted with ether (2×50 mL). The extract was washed with saturated sodium chloride and then dried over anhydrous Na2SO4. Evaporation of ether followed by flash chromatography using 2% ethyl acetate in hexane afforded 1-(2,4-difluorophenyl)-2-(3,5-d-imethoxy-4-1-propylphenyl)ethene (31) quantitatively as a yellowish crystal. 1HNMR (CDCl3, ppm): δ 1.32 (d, J=7.1 Hz, 6H), 3.63 (qint, J=7.1 Hz, 1H), 3.90 (s, 6H), 6.76 (s, 2H), 7.08 (d, J=17 Hz, 1H), 7.27 (d, J=17 Hz, 1H), 7.63 (d, J=8 Hz, 2H), 8.13 (d, J=8 Hz, 2H).

Workup

custom(6 h)
extractionextracted with ether (2×50 mL)
washThe extract was washed with saturated sodium chloride
dry with materialdried over anhydrous Na2SO4
customEvaporation of ether

Sources & evidence

ORD record: ord-9a93d779f474498bbcfdf23351e4791c
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07868047B2

Reaction notes

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