Trimethylsilylacetylene → HCID 86704323, compound

HRID 2282084Notes

Reaction equation

HRID 2282084 reaction equation
Br[C:2]1[S:6][C:5]([C:7]2[S:8][C:9]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:10][CH:11]=2)=[CH:4][CH:3]=1.[CH3:18][Si:19]([C:22]#[CH:23])([CH3:21])[CH3:20]>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.C1COCC1>[CH2:12]([C:9]1[S:8][C:7]([C:5]2[S:6][C:2]([C:23]#[C:22][Si:19]([CH3:21])([CH3:20])[CH3:18])=[CH:3][CH:4]=2)=[CH:11][CH:10]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 597524575-Bromo-5'-hexyl-2,2'-bithiophene

Product 1

HCID 86704323HCID 86704323, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Sonogashira cross coupling reaction was carried out using 5-bromo-5′-hexyl-2,2′-bithiophene (0.46 g, 1.39 mmol), trimethylsilyl acetylene (0.35 ml, 3.50 mmol), N-diisopropylethylamine (4.8 ml), Pd(PPh3)4 (80 mg, 0.070 mmol), CuI (13 mg, 0.070 mmol) and THF (10 ml), and the reaction was treated in accordance with a conventional method, thereby producing an intended product (yield: 62%).

Workup

  1. customreaction
  2. additionthe reaction was treated in accordance with a conventional method

Sources & evidence

ORD record
ord-15232a0405ed49ada42679438c4ba935
Source dataset
uspto-grants-2015_09
Patent number
US09139774B2

Reaction notes

Loading…