Cyclopropylacetylene → HCID 118021660, compound

HRID 518568Notes

Reaction equation

HRID 518568 reaction equation
Br[C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[C:4]([Br:12])[C:3]=1[OH:13].[C:14]([CH:16]1[CH2:18][CH2:17]1)#[CH:15]>N1C=CC=CC=1>[Br:12][C:4]1[C:3]2[O:13][C:14]([CH:16]3[CH2:18][CH2:17]3)=[CH:15][C:2]=2[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=1

Participants

4

Reactant 2

HCID 138823CyclopropylacetyleneHCID 8193002,6-Dibromo-4-(methylsulfonyl)phenol

Product 1

HCID 118021660HCID 118021660, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 2,6-dibromo-4-methylsulfonylphenol (1 g, 3.30 mmol) in pyridine (40 mL) was added ethynylcyclopropane (240 mg, 3.64 mmol) and Cu2O (260 mg, 1.82 mmol). The reaction mixture was degassed with N2. The mixture was heated to 130° C. for 3 hours. It was then concentrated and purified by column chromatography (PE to PE/EA=3/1) to give the title product (510 mg, 53%) as a gray solid. 1H NMR (CDCl3, 400 MHz) δ 7.99 (s, 1H), 7.93 (s, 1H), 6.52 (s, 1H), 3.07 (s, 3H), 2.13-2.11 (m, 1H), 1.13-1.05 (m, 4H).

Workup

  1. customThe reaction mixture was degassed with N2
  2. concentrationIt was then concentrated
  3. custompurified by column chromatography (PE to PE/EA=3/1)

Sources & evidence

ORD record
ord-550d37944bd44717a720a7fd08c39c35
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

Loading…