2,4'-Difluorobenzophenone → HCID 21705161, compound

HRID 1595555Notes

Reaction equation

HRID 1595555 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.[F:10][C:11]1[CH:25]=[CH:24][CH:23]=[CH:22][C:12]=1[C:13]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)=[O:14]>C(OC)(C)(C)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:13]([C:15]2[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=2)([C:12]2[CH:22]=[CH:23][CH:24]=[CH:25][C:11]=2[F:10])[OH:14])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 676512,4'-DifluorobenzophenoneHCID 178418676HCID 178418676, compound

Product 1

HCID 21705161HCID 21705161, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

p-Fluorophenylmagnesium bromide (124 mL, 0.12 mol) was added dropwise to a stirring solution of 2,4′-difluorobenzophenone (24.5 g, 0.11 mol) in t-butylmethyl ether (100 mL) at rt. After the addition was complete the reaction was heated at reflux for 3 h. The solution was then cooled to rt and was poured in to ice cold 1.0 M HCl (aq) (100 mL). The organics were extracted with EtOAc (3×70 mL) and dried (Na2SO4). Concentration under reduced pressure gave the desired product bis(4-fluorophenyl)-2-fluorophenylmethanol as a pale yellow 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 (3×70 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-d115099f9d0349fe922b8ac45d5a3ab1
Source dataset
uspto-grants-2001_09
Patent number
US06288122B1

Reaction notes

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