Water → 3,3'-(2-Phenylethene-1,1-diyl)bis((trifluoromethoxy)benzene)

HRID 1874243

Reaction equation

HRID 1874243 reaction equation
[H-].[Na+].[F:3][C:4]([F:26])([F:25])[O:5][C:6]1[CH:7]=[C:8]([C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]([F:24])([F:23])[F:22])[CH:15]=2)=O)[CH:9]=[CH:10][CH:11]=1.[CH2:27](P(=O)(OCC)OCC)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O>C1COCC1.C1OCCOCCOCCOCCOC1>[C:28]1([CH:27]=[C:12]([C:14]2[CH:15]=[C:16]([O:20][C:21]([F:24])([F:23])[F:22])[CH:17]=[CH:18][CH:19]=2)[C:8]2[CH:7]=[C:6]([O:5][C:4]([F:26])([F:25])[F:3])[CH:11]=[CH:10][CH:9]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14122Diethyl benzylphosphonateHCID 24758Sodium hydrideHCID 59458637Bis(3-(trifluoromethoxy)phenyl)methanone

Product 1

HCID 594586043,3'-(2-Phenylethene-1,1-diyl)bis((trifluoromethoxy)benzene)Yield 53%

Reagents, catalysts & solvents 2

HCID 3633615-Crown-5CatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of NaH (60% in oil, 0.24 g, 6 mmol) in dry THF (25 mL) under nitrogen was added 15-crown-5 (0.06 g). The suspension was cooled in an ice bath. Bis(3-(trifluoromethoxy)phenyl)methanone (2.10 g, 6 mmol) and diethyl benzylphosphonate (1.37 g, 6 mmol) were dissolved in THF (12 mL) and added to the suspension. The reaction mixture was stirred at ice bath temperature for 15 min, allowed to warm to rt and stirred overnight. The reaction mixture was poured into water and extracted with ether (2×). The combined ether layers were washed with 10% NaHSO3, sat. NaCl, dried over K2CO3, filtered and purified by ISCO using a gradient of 0-4% EtOAc/hexanes as eluent to give 3,3′-(2-phenylethene-1,1-diyl)bis((trifluoromethoxy)benzene) as a colorless oil (1.34 g, 53% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.33 (m, 2H), 7.2-7.1 (m, 8H), 7.04 (s, 1H), 7.0-6.97 (m, 3H).

Workup

  1. temperatureThe suspension was cooled in an ice bath
  2. additionadded to the suspension
  3. stirringstirred overnight
  4. extractionextracted with ether (2×)
  5. washThe combined ether layers were washed with 10% NaHSO3, sat. NaCl
  6. dry with materialdried over K2CO3
  7. filtrationfiltered
  8. custompurified by ISCO

Sources & evidence

ORD record
ord-59f5cfe8f98c4ca6bc58b24e9fda190f
Source dataset
uspto-grants-2012_11
Patent number
US08304403B2

Linked notes

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