Hydrochloric Acid → 4-Chloro-2-{[2-methyl-5-(propylsulfonyl)phenyl]ethynyl}phenol

HRID 2390316Notes

Reaction equation

HRID 2390316 reaction equation
[CH2:1]([S:4]([C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]([C:14]#[C:15][C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=2[O:23]COC)[CH:8]=1)(=[O:6])=[O:5])[CH2:2][CH3:3].Cl>O1CCOCC1>[Cl:22][C:20]1[CH:19]=[CH:18][C:17]([OH:23])=[C:16]([C:15]#[C:14][C:9]2[CH:8]=[C:7]([S:4]([CH2:1][CH2:2][CH3:3])(=[O:6])=[O:5])[CH:12]=[CH:11][C:10]=2[CH3:13])[CH:21]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 585220943-{[5-Chloro-2-(methoxymethoxy)phenyl]ethynyl}-4-methylphenyl propyl sulfone2×

Product 1

HCID 565939734-Chloro-2-{[2-methyl-5-(propylsulfonyl)phenyl]ethynyl}phenolYield 91.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-{[5-Chloro-2-(methoxymethoxy)phenyl]ethynyl}-4-methylphenyl propyl sulfone (Intermediate 266; 1.09 g; 2.77 mmol) was treated with a 4 N solution hydrogen chloride in 1,4-dioxane (21 ml) and stirred at RT for 7 hours. The reaction mixture was concentrated to dryness under reduced pressure to afford the title compound as a beige solid (884 mg; 91%).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-1f7073a08b554d329347cb879fdb7ddd
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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