Propargyl bromide → 1-(Methylsulfonyl)-4-(prop-2-ynyloxy)benzene

HRID 1928598Notes

Reaction equation

HRID 1928598 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH2:12](Br)[C:13]#[CH:14].C([O-])([O-])=O.[K+].[K+]>>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:14][C:13]#[CH:12])=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

4

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 1233504-(Methylsulfonyl)phenol

Product 1

HCID 577083901-(Methylsulfonyl)-4-(prop-2-ynyloxy)benzene

Procedure

A mixture of 4-methylsulfonyl-phenol, propargyl bromide and K2CO3 was refluxed overnight. After cooling, the mixture was filtered through a pad of celite. The filtrate was concentrated in vacuo. The crude solid product was purified on silica gel to give the desired product as a pale yellow solid. 1H NMR (CDCl3): δ 7.9 (2H, d), 7.12 (2H, d), 4.79 (2H, d), 3.05 (3H, s), 2.58 (1H, t).

Workup

  1. temperaturewas refluxed overnight
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered through a pad of celite
  4. concentrationThe filtrate was concentrated in vacuo
  5. customThe crude solid product was purified on silica gel

Sources & evidence

ORD record
ord-0b499538489f423a85c8c5da844d13ca
Source dataset
uspto-grants-2012_05
Patent number
US08183381B2

Reaction notes

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