Water → HCID 67983834, compound

HRID 1525467Notes

Reaction equation

[C:1]([C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH:10]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:11]2=[O:14])=[CH:7][C:6]=1[O:19][CH3:20])([CH3:4])([CH3:3])[CH3:2].C([O-])(=O)C.[K+].O.[Br:27]Br>[N+](CC)(CC)(CC)CC.[I-].ClCCl>[Br:27][C:7]1[C:6]([O:19][CH3:20])=[C:5]([C:1]([CH3:2])([CH3:4])[CH3:3])[CH:13]=[C:12]2[C:8]=1[CH2:9][CH:10]([CH2:15][CH:16]([CH3:17])[CH3:18])[C:11]2=[O:14]

Participants

Conditions

Temperature: 5 °C

Procedure

To a mixture of 24.9 g (90.9 mmol) of 6-tert-butyl-2-isobutyl-5-methoxyindan-1-one, 25.8 g of potassium acetate, 0.5 g of Et4NI, 50 ml of dichloromethane and 150 ml of water 4.66 ml (14.5 g, 90.9 mmol) of bromine was added dropwise by vigorous stirring at 5° C. for 5 min. This mixture was stirred at 5° C. for 3 h, then 15.2 g of potassium acetate was added, and finally 2.56 ml (8.24 g, 51.6 mmol) of bromine was added. The resulting mixture was additionally stirred at this temperature for 1 h. and then washed by aqueous Na2SO3 to remove an excess of bromine. The product was extracted by 3×150 ml of dichloromethane, The combined organic extract was dried over K2CO3, evaporated to dryness, and the residue was dried in vacuum. This procedure gave 31.9 g (99%) of yellowish crystalline material which was further used without an additional purification.

Workup

additionwas added dropwise
stirringThis mixture was stirred at 5° C. for 3 h
stirringThe resulting mixture was additionally stirred at this temperature for 1 h.
washwashed by aqueous Na2SO3
customto remove an excess of bromine
extractionThe product was extracted by 3×150 ml of dichloromethane
extractionThe combined organic extract
dry with materialwas dried over K2CO3
customevaporated to dryness
customthe residue was dried in vacuum

Sources & evidence

ORD record: ord-c19bfc0dd03d4b44a4e6afde60c62b98
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079985B2

Reaction notes

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