Bromine → HCID 178523765, compound

HRID 2273219Notes

Reaction equation

HRID 2273219 reaction equation
[Br:1]Br.[CH2:3]([O:10][C:11](=[O:22])[NH:12][C@H:13]1[CH2:18][CH2:17][C@H:16]([C:19](=[O:21])[CH3:20])[CH2:15][CH2:14]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO>[CH2:3]([O:10][C:11](=[O:22])[NH:12][C@H:13]1[CH2:18][CH2:17][C@H:16]([C:19](=[O:21])[CH2:20][Br:1])[CH2:15][CH2:14]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 178468180HCID 178468180, compound

Product 1

HCID 178523765HCID 178523765, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
10 °C

Procedure

Bromine (160 μL, 3.12 mmol, 1.0 eq) is added at 10° C. to a stirred solution of (trans-4-acetyl-cyclohexyl)-carbamic acid benzyl ester (850 mg, 3.12 mmol, 1.0 eq) in methanol (30 mL). After 4 hours stirring at 10° C., the reaction mixture is diluted with petroleum ether (15 mL) and the resulting precipitate is collected by filtration to afford [trans-4-(2-bromo-acetyl)-cyclohexyl]-carbamic acid benzyl ester as a white solid (920 mg, 83% yield).

Workup

  1. filtrationthe resulting precipitate is collected by filtration

Sources & evidence

ORD record
ord-88ee12094df4459e932117b218b63fe0
Source dataset
uspto-grants-2015_09
Patent number
US09120822B2

Reaction notes

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