Ethyl Acetate → HCID 86685061, compound

HRID 532175Notes

Reaction equation

HRID 532175 reaction equation
Br[C:2]1[CH:3]=[C:4]([Cl:10])[C:5]([Cl:9])=[C:6]([Cl:8])[CH:7]=1.[CH3:11][C:12]1(C)[C:16](C)(C)OB(C(C)=C)O1.C([O-])([O-])=O.[K+].[K+].CC(=O)OCC>C1COCC1.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:10][C:4]1[CH:3]=[C:2]([C:12]([CH3:16])=[CH2:11])[CH:7]=[C:6]([Cl:8])[C:5]=1[Cl:9]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 41244005-bromo-1,2,3-trichlorobenzeneHCID 109974264,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane

Product 1

HCID 86685061HCID 86685061, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 5-bromo-1,2,3-trichlorobenzene (3.64 g, 14 mmol), 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (2.5 g, 15 mmol) and Pd(PPh3)2Cl2 (983 mg, 1.4 mmol) in THF (50 ml) and H2O (5 ml) at rt was added K2CO3 (5.8 g, 42 mmol). The mixture was refluxed overnight and then concentrated under reduced pressure. The residue was purified by column chromatography over silica gel eluted with PE:EA (5:1 to 2:1) to give the desired intermediate (2.5 g, yield 81%) as a yellow oil: 1H NMR (300 MHz, CDCl3): δ 7.44 (s, 2H), 5.39 (s, 1H), 5.19-5.18 (t, 1H), 2.10 (s, 3H) ppm.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by column chromatography over silica gel
  4. washeluted with PE

Sources & evidence

ORD record
ord-b63777b2504d44adb78d7c4a1668bb87
Source dataset
uspto-grants-2014_10
Patent number
US08853186B2

Reaction notes

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