1-Ethynyl-4-fluorobenzene → HCID 69518018, compound

HRID 854996Notes

Reaction equation

HRID 854996 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]([C:18]([F:21])([F:20])[F:19])[O:8][C:9]2[C:14]([CH:15]=1)=[CH:13][C:12]([Cl:16])=[CH:11][C:10]=2I)=[O:5])[CH3:2].[C:22]([C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)#[CH:23]>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.[Cu]I>[CH2:1]([O:3][C:4]([C:6]1[CH:7]([C:18]([F:21])([F:20])[F:19])[O:8][C:9]2[C:14]([CH:15]=1)=[CH:13][C:12]([Cl:16])=[CH:11][C:10]=2[CH2:23][CH2:22][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 5226271-Ethynyl-4-fluorobenzeneHCID 21883552ethyl 6-chloro-8-iodo-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Product 1

HCID 69518018HCID 69518018, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

To 0.350 g (0.809 mmole) of ethyl-6-chloro-8-iodo-2-(trifluoromethyl)-2H-chromene-3-carboxylate was added 47 mg (0.040 mmole) tetrakis(triphenylphosphine)palladium(0), 15 mg (0.081 mmole) copper (I) iodide, 5mL degassed toluene, 0.338 mL (2.43 mmole) degassed TEA, and 0.139 mL (1.21 mmole)1-ethynyl-4-fluorobenzene. The mixture was stirred overnight at room temperature. The mixture was concd and the resulting oil was purified using reverse phase chromatography to afford a crystalline solid. MS (ES+) 425 (M+1, 100).

Workup

  1. customdegassed toluene, 0.338 mL (2.43 mmole)
  2. customthe resulting oil was purified
  3. customto afford a crystalline solid

Sources & evidence

ORD record
ord-edd9018a8d2943828fc791b7735fbb26
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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