Water → 1-(1-(4-(Benzyloxy)phenyl)vinyl)-2-fluorobenzene

HRID 2174429Notes

Reaction equation

HRID 2174429 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24][Mg+].[Br-].OS(O)(=O)=O.O>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])=[CH2:24])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 57701069(4-Benzyloxy-phenyl)-2-fluorophenyl-methanoneHCID 178418689HCID 178418689, compound

Product 1

HCID 894003491-(1-(4-(Benzyloxy)phenyl)vinyl)-2-fluorobenzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Compound 1 (4.0 g, 13.1 mmol) was dissolved in dry THF (40 mL) and the solution was cooled to 0° C. CH3MgBr (15 mL, 19.5 mmol, 1.3 M) was added drop-wise. The resulting mixture was stirred at room temperature overnight. The solution was cooled to 0° C. and H2SO4 (2 mL, 98%) was added. A precipitate was formed and the inhomogeneous mixture was stirred at room temperature for 1 h. H2O (20 mL) was added and the mixture was extracted with diethyl ether (2×100 mL). The organic phase was washed with NaHCO3 (2×50 mL, saturated aqueous solution) and brine (50 mL) and dried over Na2SO4. Filtration and evaporation of the solvent under reduced pressure gave a crude material which was purified by column chromatography (heptane:ethyl acetate 6:1). Yield 2.58 g, 65% as an off-white solid. 1H-NMR (CDCl3) δ; 7.46-7.36 (m, 4H), 7.36 (m, 5H), 7.18-7.03 (m, 2H), 6.93 (d, 2H, J=8.6 Hz), 5.68 (d, 1H, J=1.0 Hz), 5.32 (s, 1H), 5.07 (s, 2H); 13C-NMR (CDCl3) δ 160.1 (d, J=248 Hz), 158.6, 143.5, 137.0, 133.4, 131.5 (d, J=3.5 Hz), 129.2 (d, J=8.1 Hz), 128.6 (2C), 128.0 (4C), 127.5 (2C), 123.9 (d, J=3.8 Hz), 115.7 (d, J=22.3 Hz), 115.3 (d, J=1.9 Hz), 114.6 (2C), 70.0.

Workup

  1. temperatureThe solution was cooled to 0° C.
  2. customA precipitate was formed
  3. stirringthe inhomogeneous mixture was stirred at room temperature for 1 h
  4. extractionthe mixture was extracted with diethyl ether (2×100 mL)
  5. washThe organic phase was washed with NaHCO3 (2×50 mL, saturated aqueous solution) and brine (50 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationFiltration and evaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-5482af0a297f438a8f91347ef34dc266
Source dataset
uspto-grants-2015_06
Patent number
US09061981B2

Reaction notes

Loading…