4,4'-Difluorobenzophenone → Ethyl 3,3-bis(4-fluorophenyl)acrylate

HRID 2190299Notes

Reaction equation

HRID 2190299 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)=O)=[CH:20][CH:19]=1>C1(C)C=CC=CC=1.CCOCC>[F:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 95824,4'-DifluorobenzophenoneHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydride

Product 1

HCID 21908058Ethyl 3,3-bis(4-fluorophenyl)acrylate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of sodium hydride (60% weight dispersion in mineral oil, 1.35 g, 33.8 mmol) in PhMe (35 mL) at 0° C. was added ethyl 2-(diethoxyphosphoryl)acetate (7.57 g, 33.8 mmol, 6.7 mL). The reaction mixture was stirred at 0° C. for 20 min and a solution of bis(4-fluorophenyl)methanone (5.65 g, 25.9 mmol) in PhMe (35 mL) was added. The reaction mixture was warmed to room temperature, stirred for 1 h, and heated to 50° C. for 3 d. The reaction mixture was diluted with Et2O, washed with water (2×), brine (1×), dried over MgSO4, filtered, and concentrated to give ethyl 3,3-bis(4-fluorophenyl)acrylate which was used in the next step without further purification.

Workup

  1. temperatureThe reaction mixture was warmed to room temperature
  2. stirringstirred for 1 h
  3. temperatureheated to 50° C. for 3 d
  4. washwashed with water (2×), brine (1×)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0f02772f5bf24a4882de85084b110fd6
Source dataset
uspto-grants-2012_12
Patent number
US08324396B2

Reaction notes

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