Sodium Carbonate → 1,2,3-Trifluoro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene

HRID 532198Notes

Reaction equation

HRID 532198 reaction equation
[F:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[C:6]([F:9])[C:7]=1[F:8].Br[C:14]([C:16]([F:19])([F:18])[F:17])=[CH2:15].C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.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]>[F:1][C:2]1[CH:3]=[C:4]([C:14]([C:16]([F:19])([F:18])[F:17])=[CH2:15])[CH:5]=[C:6]([F:9])[C:7]=1[F:8]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2726961-Propene, 2-bromo-3,3,3-trifluoro-HCID 2734671(3,4,5-Trifluorophenyl)boronic Acid (contains varying amounts of Anhydride)

Product 1

HCID 866850701,2,3-Trifluoro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of (3,4,5-trifluorophenyl)boronic acid (0.5 g, 2.84 mmol), 2-bromo-3,3,3-trifluoroprop-1-ene (596 mg., 3.41 mmol, 1.2 eq), Na2CO3 (0.90 g, 8.52 mmol, 3 eq) and Pd(dppf)Cl2 (232 mg, 10% mol) in DME (20 mL) and water (2 mL) was heated at 70 to 80° C. for 2 h. The mixture was cooled to 0° C. with ice-water bath, and then used to next step without further purification.

Workup

  1. temperatureThe mixture was cooled to 0° C. with ice-water bath
  2. customused to next step without further purification

Sources & evidence

ORD record
ord-372292bb21e94fb1a2a12d31fc518dbe
Source dataset
uspto-grants-2014_10
Patent number
US08853186B2

Reaction notes

Loading…