Sodium Chloride → (E)-1-chloro-2-(fluoromethylene)-4-(p-fluorophenyl)butane

HRID 1449852Notes

Reaction equation

HRID 1449852 reaction equation
C(Cl)(=O)C([Cl:4])=O.CN(C)C=O.[F:12]/[CH:13]=[C:14](\[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)/[CH2:15]O.[Cl-].[Na+]>C1(C)C=CC=CC=1>[Cl:4][CH2:15]/[C:14](=[CH:13]/[F:12])/[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 10943450(E)-2-(fluoromethylene)-4-(p-fluorophenyl)butan-1-ol

Product 1

HCID 9815806(E)-1-chloro-2-(fluoromethylene)-4-(p-fluorophenyl)butane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

Combine oxalyl chloride (2.71 g, 21.4 mmol) and toluene (20 mL). Cool to 0° C. Add N,N-dimethylformamide (1.62 g, 22.2 mmol) as a solution in toluene (2 mL). Warm to ambient temperature. After 10 minutes, cool to 0° C. Add (E)-2-(fluoromethylene)-4-(p-fluorophenyl)butan-1-ol (4.0 g, 20.2 mmol). Warm to ambient temperature. After 18 hours, pour the reaction mixture into a saturated sodium chloride solution (100 mL). Extract the aqueous layer 3 times with toluene. Dry the combined organic layers over Na2SO4, filter, and evaporate in vacuo to give the title compound. 1H NMR (CDCl3, 300 MHz) δ 2.52 (m, 2H), 2.75 (m, 2H), 3.91 (d, J=6 Hz, 2H), 6.65 (d, J=82.5 Hz, 1H), 6.95 (m, 2H), 7.15 (m, 2H).

Workup

  1. temperatureWarm to ambient temperature
  2. temperaturecool to 0° C
  3. temperatureWarm to ambient temperature
  4. waitAfter 18 hours
  5. extractionExtract the aqueous layer 3 times with toluene
  6. dry with materialDry the combined organic layers over Na2SO4
  7. filtrationfilter
  8. customevaporate in vacuo

Sources & evidence

ORD record
ord-a3771361f6c24794aafc463471762ef4
Source dataset
uspto-grants-1997_02
Patent number
US05599986

Reaction notes

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