Hydrochloric Acid → Bis(4-fluorophenyl)(phenyl)methanol

HRID 1595552Notes

Reaction equation

HRID 1595552 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][C:13]([C:14]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[O:15])=[CH:12][CH:11]=1.Cl>C(OC)(C)(C)C>[F:9][C:10]1[CH:24]=[CH:23][C:13]([C:14]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[OH:15])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 95824,4'-DifluorobenzophenoneHCID 178418255HCID 178418255, compound

Product 1

HCID 12580270Bis(4-fluorophenyl)(phenyl)methanol

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

Phenylmagnesium bromide (100 mL, 0.1 mol) was added dropwise to a stirring solution of 4,4′-difluorobenzophenone (20 g, 0.092 mol) in t-butylmethyl ether (150 mL) at rt. 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 aqueous 1.0 M HCl (100 mL). The organics were extracted with EtOAc (2×50 mL) and dried (Na2SO4). Concentration under reduced pressure gave bis(4-fluorophenyl)phenylmethanol as a pale brown oil. After drying in vacuo for 2 h the crude material 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 (2×50 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-ea4298662896447ab9e93d2f7401f237
Source dataset
uspto-grants-2001_09
Patent number
US06288122B1

Reaction notes

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