2-Methyl-4-[(4-methylbenzenesulfonyl)oxy]butan-2-ol → 4-(5-Bromo-4,6-dimethylpyridin-2-yloxy)-2-methylbutan-2-ol

Reaction equation

[Br:1][C:2]1[C:3]([CH3:10])=[CH:4][C:5]([OH:9])=[N:6][C:7]=1[CH3:8].CC1C=CC(S(O[CH2:22][CH2:23][C:24]([OH:27])([CH3:26])[CH3:25])(=O)=O)=CC=1>>[Br:1][C:2]1[C:3]([CH3:10])=[CH:4][C:5]([O:9][CH2:22][CH2:23][C:24]([CH3:26])([OH:27])[CH3:25])=[N:6][C:7]=1[CH3:8]

Participants

Reactant 2

HCID 140012952-Methyl-4-[(4-methylbenzenesulfonyl)oxy]butan-2-ol

HCID 178429301HCID 178429301, compound

Product 1

HCID 595445344-(5-Bromo-4,6-dimethylpyridin-2-yloxy)-2-methylbutan-2-olYield 70.1%

Procedure

According to a method described in [WO 2009/054423 pamphlet, (Production Example 37)], from 5-bromo-4,6-dimethyl-2-hydroxypyridine (1.50 g) and 3-hydroxy-3-methylbutyl 4-methylbenzenesulfonate (2.11 g), the subject compound (1.50 g) was obtained as a colorless oil.

Sources & evidence

ORD record: ord-743b476f845d4cebb8691bd3a5e7e018
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455500B2

Reaction notes

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