Chloride → HCID 86698846, compound

HRID 338517Notes

Reaction equation

HRID 338517 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-ced7499fdb8e4dca9262201d9773526b
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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