Ethanol → Ethyl 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(2,2,2-trifluoroethyl)benzoate

HRID 63865Notes

Reaction equation

HRID 63865 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][C:11]([C:17]3[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[C:19]([Cl:27])[CH:18]=3)([C:13]([F:16])([F:15])[F:14])[O:10][N:9]=2)=[CH:4][C:3]=1[CH2:28][C:29]([F:32])([F:31])[F:30].C[C:34]([O-:36])=[O:35].[Na+].[CH2:38](O)[CH3:39]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:27][C:19]1[CH:18]=[C:17]([C:11]2([C:13]([F:16])([F:15])[F:14])[O:10][N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([C:34]([O:36][CH2:38][CH3:39])=[O:35])=[C:3]([CH2:28][C:29]([F:32])([F:31])[F:30])[CH:4]=3)[CH2:12]2)[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 517045Sodium AcetateHCID 118047306HCID 118047306, compound

Product 1

HCID 118046612Ethyl 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(2,2,2-trifluoroethyl)benzoate

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Conditions

Temperature
110 °C

Procedure

Into a 50-mL pressure tank reactor (10 atm), was placed 3-[4-bromo-3-(2,2,2-trifluoroethyl)phenyl]-5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazole (600 mg, 1.08 mmol, 1.00 equiv), ethanol (20 mL), Pd(dppf)Cl2 (158 mg, 0.22 mmol, 0.20 equiv), NaOAc (177 mg, 2.16 mmol, 2.00 equiv), CO (10 atm). The resulting solution was stirred overnight at 110° C. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:30-1:10). This resulted in 300 mg (46%) of ethyl 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(2,2,2-trifluoroethyl)benzoate as yellow oil.

Workup

  1. customInto a 50-mL pressure tank reactor (10 atm), was placed
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. customThis resulted in 300 mg (46%) of ethyl 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(2,2,2-trifluoroethyl)benzoate as yellow oil

Sources & evidence

ORD record
ord-d5f3362be8ab4fff93f6f4f781b1ae2d
Source dataset
uspto-grants-2016_09
Patent number
US09447084B2

Reaction notes

Loading…