Chloride → HCID 86698846, compound

HRID 1054861Notes

Reaction equation

HRID 1054861 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH2:9])=[C:4]([O:10][CH3:11])[CH:3]=1.[Cl-:12].P(Cl)(Cl)([Cl:15])=O.[O:18]1CC[CH2:20][CH2:19]1>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:20][C:19](=[O:18])[C:9]2([Cl:15])[Cl:12])=[C:4]([O:10][CH3:11])[CH:3]=1

Participants

5

Reactant 4

HCID 312ChlorideHCID 8028Tetrahydrofuran2×HCID 24813Phosphorus oxychlorideHCID 66577920HCID 66577920, compound

Product 1

HCID 86698846HCID 86698846, compoundYield 35%

Procedure

To a suspension of activated Zn—Cu complex (1.4 g, 19 mmol) and 4-bromo-1-ethenyl-2-methoxybenzene (2.700 g, 12.67 mmol) in dry tetrahydrofuran (30 mL) was added dropwise through addition funnel a solution of thrichloroacetic chloride (2.11 g, 19.0 mmol) and phosphoryl chloride (11.7 ml, 12.7 mmol) in tetrahydrofuran (20 mL) during 2 hr at refluxing temperature. Then the mixture was stirred overnight under refluxing temperature. The mixture was cooled to room temperature and filtered. The filtrate was combined with ethyl acetate (100 mL), the combined solution was concentrated to give the title compound (1.45 g, 35%) which was used into next step without further purification.

Workup

  1. temperatureat refluxing temperature
  2. temperatureunder refluxing temperature
  3. filtrationfiltered
  4. concentrationthe combined solution was concentrated

Sources & evidence

ORD record
ord-8b095df7339245a0ac96e27a13d65cf9
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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