Iodine → HCID 178444243, compound

HRID 1734967Notes

Reaction equation

[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].II.[Br:20]Br.S([O-])(O)=O.[Na+]>ClCCl.[Fe].O>[Br:20][C:15]1[CH:14]=[CH:13][C:12]([C@H:9]2[CH2:8][CH2:7][C@H:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:11][CH2:10]2)=[CH:17][CH:16]=1

Participants

Conditions

Temperature: -10 °C

Procedure

In 30 ml of dichloromethane was dissolved 11.1. g of trans-4-pentylcyclohexylbenzene, and 0.1 g of iron powder and 0.05 g of iodine were added thereto. To the mixture was added dropwise 7.7 g of bromine dissolved in 20 ml of dichloromethane at 0° C. or lower. The mixture was stirred at -10° C. for 6 hours and then allowed to warm to room temperature. Water and then an aqueous solution of sodium hydrogensulfite were added to the reaction mixture, and the product was extracted with hexane. The extract was washed successively with a sodium bicarbonate aqueous solution, water and a saturated sodium chloride aqueous solution, and dried. The solvent was removed by distillation, and the resulting crude crystals were recrystallized from ethanol to give 4.8 g of 1-bromo-4-(trans-4-pentylcyclohexyl)benzene. (

Workup

temperatureto warm to room temperature
extractionthe product was extracted with hexane
washThe extract was washed successively with a sodium bicarbonate aqueous solution, water
dry with materiala saturated sodium chloride aqueous solution, and dried
customThe solvent was removed by distillation
customthe resulting crude crystals were recrystallized from ethanol

Sources & evidence

ORD record: ord-441a4ce427f446c48474f0cf722e1268
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05536443

Reaction notes

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