Sodium Hydroxide → 1-Bromo-1-(6-chloro-2-pyridinyloxy)-3,3-dimethyl-2-butanone

HRID 1862836Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([O:8][CH2:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[CH:4][CH:3]=1.[Br:16]Br.[OH-].[Na+]>O1CCOCC1>[Br:16][CH:9]([O:8][C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([Cl:1])[N:7]=1)[C:10](=[O:15])[C:11]([CH3:12])([CH3:14])[CH3:13]

Participants

Conditions

Temperature: 65 °C

Procedure

A stirred solution of 227.68 g (1.0 mole) of 1-(6-chloro-2-pyridinyloxy)-3,3-dimethyl-2-butanone, prepared above, in 1000 ml dioxane was heated to 65° C. The heat source was removed and 175.8 g (1.1 mole) bromine added dropwise. After the addition of the bromine, the solution was stirred for 10 minutes and then poured into 3 liters ice water containing 25 g sodium bisulfite. The mixture was made slightly basic with 50% NaOH and twice extracted with 500-ml portions of pentane. The pentane extracts were washed with 1000 ml of 5% NaOH and dried, giving 259 g (84% yield) of 1-bromo-1-(6-chloro-2-pyridinyloxy)-3,3-dimethyl-2-butanone. Crystallization from pentane gave a white solid melting at 50°-52° C.

Workup

customThe heat source was removed
extractiontwice extracted with 500-ml portions of pentane
washThe pentane extracts were washed with 1000 ml of 5% NaOH
customdried

Sources & evidence

ORD record: ord-6c31ce4b3f7a46bcaa0bbea423674527
Source dataset: uspto-grants-1979_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04166854

Reaction notes

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