Ammonium Chloride → (3-(1,3-Dioxolan-2-yl)phenyl)[3-(trifluoromethyl)phenyl]-methan-1-ol

HRID 130348

Reaction equation

HRID 130348 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)[CH:5]=[CH:6][CH:7]=1.[Mg].[F:14][C:15]([F:25])([F:24])[C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH:19]=[O:20].[NH4+].[Cl-]>C1COCC1>[O:9]1[CH2:10][CH2:11][O:12][CH:8]1[C:4]1[CH:3]=[C:2]([CH:19]([C:18]2[CH:21]=[CH:22][CH:23]=[C:16]([C:15]([F:14])([F:24])[F:25])[CH:17]=2)[OH:20])[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 679903-(Trifluoromethyl)benzaldehydeHCID 873062-(3-Bromophenyl)-1,3-dioxolane2×HCID 5462224Magnesium

Product 1

HCID 69255414(3-(1,3-Dioxolan-2-yl)phenyl)[3-(trifluoromethyl)phenyl]-methan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A 1.0 mL aliquot of 2-(3-bromophenyl)-1,3-dioxolane is added into magnesium (610 mg; 25 mmol) and THF (5 mL) under Argon. After the reaction is started, the residue of 2-(3-bromophenyl)-1,3-dioxolane (total: 5.73 g; 25 mmol) in THF (20 mL) is added dropwise into the reaction mixture. The resulting solution is stirred at room temp for six hours, and then at 50-60° C. for 20 hours. After the mixture is cooled, a solution of 3-(trifluoromethyl)-benzaldehyde (4.35 g; 25 mmol) in THF (20 mL) is added dropwise and the reaction is stirred at room temp for 24 hours. A saturated solution of NH4Cl (50 mL) is added and stirred for 30 minutes. The organic layer is separated and the aqueous layer is extracted with ethyl acetate (2×100 mL). The organic layers are combined and dried over anhydrous Na2SO4. The solvent is removed and the residue is purified by column chromatography on silica gel. Eluting with ethyl acetate/hexanes (20:80) provide a colorless oil (3.23 g; 40%) as (3-(1,3-dioxolan-2-yl)phenyl)[3-(trifluoromethyl)phenyl]-methan-1-ol: MS 307.0 (M−17).

Workup

  1. waitat 50-60° C. for 20 hours
  2. temperatureAfter the mixture is cooled
  3. stirringthe reaction is stirred at room temp for 24 hours
  4. stirringstirred for 30 minutes
  5. customThe organic layer is separated
  6. extractionthe aqueous layer is extracted with ethyl acetate (2×100 mL)
  7. dry with materialdried over anhydrous Na2SO4
  8. customThe solvent is removed
  9. customthe residue is purified by column chromatography on silica gel
  10. washEluting with ethyl acetate/hexanes (20:80)

Sources & evidence

ORD record
ord-d5bd1ef900304afea4d5fb5210705be1
Source dataset
uspto-grants-2008_06
Patent number
US07381736B2

Linked notes

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