Dichloromethane → 4-Bromo-6-tert-butyl-5-methoxy-2-methyl-1-indanone

HRID 716440Notes

Reaction equation

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

Participants

Conditions

Temperature: 5 °C

Procedure

To a mixture of 60.0 g (0.258 mol) of 6-tert-butyl-5-methoxy-2-methylindan-1-one, 130 g of NaOAc(H2O)3, 1.5 g of Et4NI, 220 ml of dichloromethane, and 450 ml of water cooled to 5° C. 45.0 g (0.282 mol) of bromine was added for ca. 5 min by vigorous stirring. This mixture was stirred for 1 h at 5° C., and then a solution of 60.0 g of NaOAc(H2O)3 in 200 ml of water was added. To the resulting mixture 23.5 (0.147 mmol) of bromine was added at 5° C. The resulting solution was stirred for 30 min and then Na2SO3 was added by small portions to remove an excess of bromine. The CH2Cl2-layer was separated from the top aqueous one and the latter was extracted with 2×300 ml of dichloromethane. The combined organic extract was dried over K2CO3, passed through a short layer of silica gel 60 (40-63 um) and then evaporated to dryness. The residue was dried in vacuum to give 79.9 g (99%) of the title compound which was further used without an additional purification.

Workup

stirringThe resulting solution was stirred for 30 min
customto remove an excess of bromine
customThe CH2Cl2-layer was separated from the top aqueous one
extractionthe latter was extracted with 2×300 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-e477589f238d43e0bcffd709b3663a86
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187583B2

Reaction notes

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