2-(2'-Fluorophenyl)-(4s,5s)-diphenyl-4,5-dihydroimidazole → 2-(2'-Diphenylphosphinophenyl)-(4s,5s)-diphenyl-4,5-dihydroimidazole

HRID 429508Notes

Reaction equation

HRID 429508 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([P-:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.[K+].C1COCC1.F[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]1[NH:28][C@@H:29]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C@H:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:31]=1>C1COCC1>[C:8]1([P:7]([C:4]2[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]2[NH:28][C@@H:29]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[C@H:30]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[N:31]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 207050562-(2'-Fluorophenyl)-(4s,5s)-diphenyl-4,5-dihydroimidazoleHCID 131722995potassium diphenylphosphide THF

Product 1

HCID 207050552-(2'-Diphenylphosphinophenyl)-(4s,5s)-diphenyl-4,5-dihydroimidazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

13.9 ml of 0.5M potassium diphenylphosphide/THF (6.95 mmol, 1.1 eq.) was heated to 60° in a thermostated oil bath. To this warm solution was then added a solution of 2.00 g fluoride 8 (6.32 mmol, 1 eq.) in 5 ml THF via syringe over 2 minutes. The resulting solution was then heated at reflux for 1 hour, cooled to room temperature and quenched by the addition of 10 ml water. The resulting mixture was extracted with methylene chloride (2×25 ml), dried (MgSO4), and the solvents removed in vacuo to give an oil.

Workup

  1. temperatureThe resulting solution was then heated
  2. temperatureat reflux for 1 hour
  3. customquenched by the addition of 10 ml water
  4. extractionThe resulting mixture was extracted with methylene chloride (2×25 ml)
  5. dry with materialdried (MgSO4)
  6. customthe solvents removed in vacuo
  7. customto give an oil

Sources & evidence

ORD record
ord-f6b6eeaf05974c4485a0de6fc8c167cb
Source dataset
uspto-grants-2001_11
Patent number
US06316620B1

Reaction notes

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