2,4'-Difluorobenzophenone → Flutrimazole carbinol

HRID 1595550Notes

Reaction equation

HRID 1595550 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:9][C:10]1[CH:24]=[CH:23][CH:22]=[CH:21][C:11]=1[C:12]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)=[O:13]>C(OC)(C)(C)C>[F:9][C:10]1[CH:24]=[CH:23][CH:22]=[CH:21][C:11]=1[C:12]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[OH:13]

Participants

4

Reactant 2

HCID 676512,4'-DifluorobenzophenoneHCID 178418255HCID 178418255, compound

Product 1

HCID 14579819Flutrimazole carbinol

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

Phenylmagnesium bromide (1.83 mL, 5.5 mmol) was added dropwise to a tirring solution of 2,4′-difluorobenzophenone (1.09 g, 5.0 mmol) in t-butylmethyl ether (12 mL) at room temperature (“rt,”˜25° C.). After the addition was complete the reaction was heated at reflux for 3 h. The solution was cooled to rt and was poured in to ice cold 1.0 M HCl (aq) (20 mL). The organics were extracted with EtOAc (3×10 mL) and dried (Na2SO4). Concentration under reduced pressure gave the desired product (2-fluorophenyl)-(4-fluorophenyl)phenylmethanol as a pale brown oil which was used in the next reaction without any further purification.

Workup

  1. additionAfter the addition
  2. temperaturewas heated
  3. temperatureat reflux for 3 h
  4. extractionThe organics were extracted with EtOAc (3×10 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-3b8019db7b0e48a59521539d5c8f797d
Source dataset
uspto-grants-2001_09
Patent number
US06288122B1

Reaction notes

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