Water → HCID 67985691, compound

HRID 1525472Notes

Reaction equation

[C:1]([C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH:10]([CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])[C:11]2=[O:14])=[CH:7][C:6]=1[O:20][CH3:21])([CH3:4])([CH3:3])[CH3:2].O.O.O.C([O-])(=O)C.[Na+].O.[Br:31]Br>[N+](CC)(CC)(CC)CC.[I-].ClCCl>[Br:31][C:7]1[C:6]([O:20][CH3:21])=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:13]=[C:12]2[C:8]=1[CH2:9][CH:10]([CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])[C:11]2=[O:14]

Participants

Conditions

Temperature: 5 °C

Procedure

To a mixture of 42.4 g (0.146 mol) of 6-tert-butyl-2-(2,2-dimethylpropyl)-5-methoxy-1-indanone, 58.0 g (0.426 mol) of sodium acetate, trihydrate, 0.93 g of Et4NI, 130 ml of dichloromethane, and 250 ml of water 23.5 g (0.147 mol) of bromine was added dropwise by vigorous stirring for 5 min at 5° C. The resulting mixture was stirred for additional 1 h at this temperature. Further on, this mixture was washed by aqueous Na2SO3 to remove an excess of bromine, and then 500 ml of dichloromethane was added. The organic layer was separated, and the aqueous layer was extracted with 2×250 ml of dichloromethane. The combined organic extract was dried over K2CO3 and then evaporated to dryness to give 54.8 g of yellowish oil which crystallizes on storage at room temperature. This product was further used without an additional purification.

Workup

additionwas added dropwise
stirringThe resulting mixture was stirred for additional 1 h at this temperature
washFurther on, this mixture was washed by aqueous Na2SO3
customto remove an excess of bromine
addition500 ml of dichloromethane was added
customThe organic layer was separated
extractionthe aqueous layer was extracted with 2×250 ml of dichloromethane
extractionThe combined organic extract
dry with materialwas dried over K2CO3
customevaporated to dryness

Sources & evidence

ORD record: ord-24504079c889459f85438140cafc67f1
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079985B2

Reaction notes

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