3-Methoxypropyl 4-methylbenzenesulfonate → 2-Chloro-6-fluoro-4-(3-methoxy-propoxy)-benzylalcohol

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[C:6]([F:10])[C:7]=1[CH2:8][OH:9].[CH3:12][O:13][CH2:14][CH2:15][CH2:16]OS(C1C=CC(C)=CC=1)(=O)=O>>[Cl:1][C:2]1[CH:3]=[C:4]([O:11][CH2:16][CH2:15][CH2:14][O:13][CH3:12])[CH:5]=[C:6]([F:10])[C:7]=1[CH2:8][OH:9]

Participants

Reactant 2

HCID 135229883-Methoxypropyl 4-methylbenzenesulfonate

HCID 222200093-Chloro-5-fluoro-4-(hydroxymethyl)phenol

Product 1

HCID 222199942-Chloro-6-fluoro-4-(3-methoxy-propoxy)-benzylalcoholYield 90%

Procedure

This compound was prepared from 3-chloro-5-fluoro-4-hydroxymethyl-phenol and toluene-4-sulfonic acid 3-methoxy-propyl ester according to the procedure described in Example 179 to give the product as a yellowish oil (382 mg, 90%); MS (EI): 248.1 (M)+.

Sources & evidence

ORD record: ord-405fb21d16b84870a96b17efc960ac1d
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07022707B2

Reaction notes

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