Pivaloyl chloride → 2-Bromo-2,2-difluoroethyl pivalate

HRID 558043Notes

Reaction equation

HRID 558043 reaction equation
[Br:1][C:2]([F:6])([F:5])[CH2:3][OH:4].[C:7](Cl)(=[O:12])[C:8]([CH3:11])([CH3:10])[CH3:9]>>[C:7]([O:4][CH2:3][C:2]([Br:1])([F:6])[F:5])(=[O:12])[C:8]([CH3:11])([CH3:10])[CH3:9]

Participants

3

Reactant 2

HCID 62493Pivaloyl chlorideHCID 183684762-Bromo-2,2-difluoroethan-1-ol

Product 1

HCID 578173452-Bromo-2,2-difluoroethyl pivalate

Procedure

One exemplary compound may be synthesized by reacting 2-bromo-2,2-difluoroethanol with pivalic chloride or anhydride to form 2-bromo-2,2-difluoroethyl pivalate, converting the bromo group into sodium sulfinate using a sulfur compound such as sodium dithionite, and converting sulfinic acid into sulfonic acid using an oxidizing agent such as hydrogen peroxide. This is followed by cation exchange with a triarylsulfonium halide or the like. The pivalic ester is then subjected to alkaline hydrolysis. Through reaction with (meth)acrylic anhydride, the alcohol resulting from hydrolysis is converted into a (meth)acrylic derivative, yielding the end compound.

Workup

  1. customOne exemplary compound may be synthesized

Sources & evidence

ORD record
ord-ba1c2c63eb094364b4d5f58f402340dc
Source dataset
uspto-grants-2011_11
Patent number
US08062828B2

Reaction notes

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