Dichloromethane → HCID 71230813, compound

HRID 716474Notes

Reaction equation

[CH2:1]([O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][C:14]=1[C:15]([CH3:18])([CH3:17])[CH3:16])[C:11](=[O:19])[CH:10]([CH3:20])[CH2:9]2)[CH:2]([CH3:4])[CH3:3].CC([O-])=O.[Na+].ClCCl.[Br:29]Br.[O-]S([O-])=O.[Na+].[Na+]>[I-].C([N+](CC)(CC)CC)C.O>[Br:29][C:7]1[C:6]([O:5][CH2:1][CH:2]([CH3:4])[CH3:3])=[C:14]([C:15]([CH3:17])([CH3:16])[CH3:18])[CH:13]=[C:12]2[C:8]=1[CH2:9][CH:10]([CH3:20])[C:11]2=[O:19]

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 91.9 g (335 mmol) of 5-isobutoxy-6-tert-butyl-2-methylindanone, 82.5 g (1.0 mol) of NaOAc, 1.70 g (7.0 mmol) of tetraethylammonium iodide, 500 ml of water, and 170 ml of dichloromethane 17.2 ml (335 mmol) of bromine was added by vigorous stirring for 1 h at 0° C. The resulting mixture was stirred for 1 h at this temperature, and then 41.3 g (0.5 mol) of NaOAc was added. To the obtained mixture 9.0 ml (175 mmol) of bromine was added dropwise for 0.5 h at 0° C. The formed mixture was stirred for 2 h at 0° C., then Na2SO3 was added to remove an excess of bromine. The organic layer was separated, dried over Na2SO4, and then evaporated to dryness. This procedure gave 116 g (98%) of the title product which was further used without an additional purification.

Workup

additionwas added
stirringThe resulting mixture was stirred for 1 h at this temperature
stirringThe formed mixture was stirred for 2 h at 0° C.
customto remove an excess of bromine
customThe organic layer was separated
dry with materialdried over Na2SO4
customevaporated to dryness

Sources & evidence

ORD record: ord-8f55ad9b6a7648d98a4cee92e011fc9d
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187583B2

Reaction notes

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