Hydrochloric Acid → HCID 178444306, compound

HRID 274165Notes

Reaction equation

HRID 274165 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]#[CH:19])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].C(C1C=CC=CC=1)(=O)C.P(Cl)(Cl)(Cl)(Cl)Cl.[F:35][CH:36]([F:45])[O:37][C:38]1[CH:43]=[CH:42][C:41](I)=[CH:40][CH:39]=1.Cl>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.C(N(CC)CC)C>[F:35][CH:36]([F:45])[O:37][C:38]1[CH:43]=[CH:42][C:41]([C:19]#[C:18][C:15]2[CH:14]=[CH:13][C:12]([C@H:9]3[CH2:8][CH2:7][C@H:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:11][CH2:10]3)=[CH:17][CH:16]=2)=[CH:40][CH:39]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 7410AcetophenoneHCID 24819Phosphorus pentachlorideHCID 27370081-(Difluoromethoxy)-4-iodobenzeneHCID 178436318HCID 178436318, compound

Product 1

HCID 178444306HCID 178444306, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

A solution of 15.3 g of 4-(trans-4-pentylcyclohexyl)phenylacetylene (available from the acetophenone by dehydration, using PCl5 /KOT), 16.2 g of difluoromethoxy-4-iodobenzene, 100 ml of triethylamine, 0.085 g of bis(triphenylphosphine)dichloropalladium and 0.11 g of copper(I) iodide is stirred at room temperature for 3 hours. The cloudy mixture is stirred into dilute hydrochloric acid (500 ml of water +200 ml of 37% hydrochloric acid), extracted with t-butyl methyl ether and worked up as usual. m.p.: 62° C., c.p.: 203.1° C.

Workup

  1. extractionextracted with t-butyl methyl ether
  2. custom203.1° C.

Sources & evidence

ORD record
ord-d747d02d422b4ca18740343545cc522e
Source dataset
uspto-grants-1995_02
Patent number
US05389292

Reaction notes

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