Nitrogen → HCID 86685071, compound

HRID 1750820Notes

Reaction equation

HRID 1750820 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](B2OC(C)(C)C(C)(C)O2)[CH:5]=[C:6]([Br:9])[C:7]=1[F:8].Br[C:20]([C:22]([F:25])([F:24])[F:23])=[CH2:21].C([O-])([O-])=O.[K+].[K+].N#N>C1COCC1.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]>[Br:9][C:6]1[CH:5]=[C:4]([C:20]([C:22]([F:25])([F:24])[F:23])=[CH2:21])[CH:3]=[C:2]([Br:1])[C:7]=1[F:8]

Participants

8

Reactant 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 2726961-Propene, 2-bromo-3,3,3-trifluoro-HCID 86685072HCID 86685072, compound

Product 1

HCID 86685071HCID 86685071, compoundYield 36.4%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(3,5-dibromo-4-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (300 mg, 0.79 mmol), 2-bromo-3,3,3-trifluoroprop-1-ene (207 mg, 1.18 mmol), Pd(dppf)Cl2 (112 mg, 0.16 mmol), K2CO3 (218 mg, 1.58 mmol) in THF (2 mL) and water (1 mL) was heated at 80° C. in a sealed vial under N2 atmosphere for 12 h, cooled to rt, quenched with water, extracted with EA (3×10 mL). The combined organic layer was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography eluted with PE to give 1,3-dibromo-2-fluoro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (100 mg, yield 30%) as solid.

Workup

  1. customquenched with water
  2. extractionextracted with EA (3×10 mL)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography
  8. washeluted with PE

Sources & evidence

ORD record
ord-dade37a4e8d64621898d2b19cb750aa3
Source dataset
uspto-grants-2015_10
Patent number
US09156860B2

Reaction notes

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