Ammonium Chloride → HCID 13007271, compound

HRID 2271278Notes

Reaction equation

HRID 2271278 reaction equation
[C:1]([O:5][C:6]1[CH:11]=[CH:10][C:9](I)=[C:8]([F:13])[C:7]=1[F:14])([CH3:4])([CH3:3])[CH3:2].[I-].[F:16][C:17]([Zn+])=[C:18]([F:20])[F:19].[Cl-].[NH4+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1COCC1>[C:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:17]([F:16])=[C:18]([F:20])[F:19])=[C:8]([F:13])[C:7]=1[F:14])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 13007270HCID 13007270, compoundHCID 178506053HCID 178506053, compound

Product 1

HCID 13007271HCID 13007271, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

A 1-liter reactor was charged with 31.2 g (0.10 mol) of 4-tert-butoxy-2,3-difluoro-1-iodobenzene and 100 ml of THF and heated at 60° C. To the reactor, 1.16 g (1 mmol) of tetrakis(triphenylphosphine)palladium(0) was added, then 300 ml of a THF solution of 1 M trifluorovinyl zinc iodide was added dropwise. After the completion of dropwise addition, the reaction solution was ripened for 30 minutes and poured into a saturated ammonium chloride aqueous solution. From the solution, a crude product was extracted with ethyl acetate in a conventional way. It was purified by silica gel chromatography, obtaining 21.5 g (yield 81%) the end product.

Workup

  1. additionAfter the completion of dropwise addition
  2. extractionFrom the solution, a crude product was extracted with ethyl acetate in a conventional way
  3. customIt was purified by silica gel chromatography

Sources & evidence

ORD record
ord-cd0dec0ea75a4a7db0dfacee3bbdc6b8
Source dataset
uspto-grants-2001_12
Patent number
US06333436B1

Reaction notes

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