Triethyl phosphite → HCID 15341134, compound

HRID 1720856Notes

Reaction equation

HRID 1720856 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[CH:6](Br)[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=1.[P:23]([O:30]CC)([O:27][CH2:28][CH3:29])[O:24][CH2:25][CH3:26]>>[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([CH:6]([P:23](=[O:30])([O:27][CH2:28][CH3:29])[O:24][CH2:25][CH3:26])[C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=2)[CH:18]=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 22416503HCID 22416503, compound

Product 1

HCID 15341134HCID 15341134, compound

Procedure

A solution containing 3,3'-bis(trifluoromethyl)benzhydryl bromide (29.8 g, 77.6 mmol), prepared according to methods in Example 3 and triethyl phosphite (21.6 mL, 126 mmol), was heated at 155°-160° C. for 16 hours, under N2. The reaction mixture was cooled and washed with H2O (2×150 mL) to remove the excess triethyl phosphite. The non-aqueous portion was added to CH2Cl2 (150 mL), dried (MgSO4), filtered, and concentrated in volume to give a pale yellow oil, 30.1 g. The crude product was chromatographed on a silica gel column. Elution with ethyl acetate/hexane (1:1) afforded analytically pure product as a white solid, 10.7 g, (31.2%), mp 82°-85° C. 300MHz 1H NMR (CDCl3): δ,4.54 (d,1H, J=25.3 Hz, PCH). MS: 441 (M+1).

Workup

  1. customprepared
  2. temperaturewas heated at 155°-160° C. for 16 hours, under N2
  3. temperatureThe reaction mixture was cooled
  4. washwashed with H2O (2×150 mL)
  5. customto remove the excess triethyl phosphite
  6. additionThe non-aqueous portion was added to CH2Cl2 (150 mL)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in volume
  10. customto give a pale yellow oil, 30.1 g
  11. customThe crude product was chromatographed on a silica gel column
  12. washElution with ethyl acetate/hexane (1:1)
  13. customafforded analytically pure product as a white solid, 10.7 g, (31.2%), mp 82°-85° C

Sources & evidence

ORD record
ord-6d776925565b4f82a8deec6f834fd287
Source dataset
uspto-grants-1996_04
Patent number
US05508273

Reaction notes

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