Nitrogen → HCID 86685067, compound

HRID 532195Notes

Reaction equation

HRID 532195 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[Cl: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[Cl:8]

Participants

8

Reactant 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 2726961-Propene, 2-bromo-3,3,3-trifluoro-HCID 86685068HCID 86685068, compound

Product 1

HCID 86685067HCID 86685067, compoundYield 56.1%

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-chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (260 mg, 0.66 mmol), 2-bromo-3,3,3-trifluoroprop-1-ene (172 mg, 0.98 mmol), Pd(dppf)Cl2 (91 mg, 0.13 mmol), K2CO3 (182 mg, 1.32 mmol) in THF (2 mL) and water (0.5 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-chloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (135 mg, yield 56%) as oil.

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-a858590ab3594c259aad257af922d962
Source dataset
uspto-grants-2014_10
Patent number
US08853186B2

Reaction notes

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