P-Cresol → 1-Chloromethanesulfonyl-4-(p-tolyloxy)-benzene

HRID 1716308Notes

Reaction equation

[Cl:1][CH2:2][S:3]([C:6]1[CH:11]=[CH:10][C:9](F)=[CH:8][CH:7]=1)(=[O:5])=[O:4].[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+]>CC(N(C)C)=O.CCOC(C)=O.O>[Cl:1][CH2:2][S:3]([C:6]1[CH:11]=[CH:10][C:9]([O:20][C:17]2[CH:18]=[CH:19][C:14]([CH3:13])=[CH:15][CH:16]=2)=[CH:8][CH:7]=1)(=[O:5])=[O:4]

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of 1-chloromethanesulfonyl-4-fluoro-benzene (0.5 g, 2.4 mmol) from Step A, 4-methyl-phenol (0.21 mL, 2.0 mmol) and K2CO3 (0.55 g, 4.0 mmol) in dry DMA (10 mL) was heated at 95° C. overnight. The reaction mixture was diluted with EtOAc and water. After the usual work-up, crude product was purified by chromatography (silica gel, 25% EtOAc/hexanes). MS 319 (M+H)+.

Workup

customAfter the usual work-up, crude product was purified by chromatography (silica gel, 25% EtOAc/hexanes)

Sources & evidence

ORD record: ord-24c16028d9694a67a62658e6fc25272c
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07803793B2

Reaction notes

Loading…