Phenylacetylene → HCID 58934840, compound

HRID 855002Notes

Reaction equation

HRID 855002 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]1([C:28]#[CH:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>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>[Cl:16][C:12]1[CH:13]=[C:14]2[C:9](=[C:10]([C:29]#[C:28][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:11]=1)[O:8][CH:7]([C:18]([F:21])([F:20])[F:19])[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:15]2

Participants

5

Reactant 2

HCID 10821PhenylacetyleneHCID 21883552ethyl 6-chloro-8-iodo-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Product 1

HCID 58934840HCID 58934840, compoundYield 88%

Reagents, catalysts & solvents 2

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

Procedure

To 2.000 g (4.624 mmole) of ethyl-6-chloro-8-iodo-2-(trifluoromethyl)-2H-chromene-3-carboxylate was added 267 mg (0.231 mmole) tetrakis(triphenylphosphine)palladium(0), 88 mg (0.462 mmole) copper (I) iodide, 40 mL degassed toluene, 1.930 mL (13.87 mmole) degassed TEA, and 0.762 mL (6.94 mmole) phenylacetylene. The mixture was stirred overnight at room temperature. The mixture was concd and the resulting oil was purified using reverse phase chromatography to afford 1.648 g (88%) of a yellow crystalline solid: 1H NMR (CDCl3/400 MHz) 1.35 (t, 3H, J=7.2 Hz), 4.27-4.39 (m, 2H), 5.83 (q, 1H, J=6.4 Hz), 7.17 (d, 1H, J=2.4 Hz), 7.34-7.37 (m, 3H), 7.45 (d, 1H, J=2.4 Hz), 7.51-7.55 (m, 2H), 7.63 (s, 1H); MS (ES+) 407 (M+1, 100); MS (EI) 406 (M+, 39), 337 (100), 309 (45).

Workup

  1. customdegassed toluene, 1.930 mL (13.87 mmole)
  2. customthe resulting oil was purified

Sources & evidence

ORD record
ord-51879b45f84347c98fd57577b9c7d2a0
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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