1,6-Dibromohexane → HCID 178523821, compound

HRID 25564Notes

Reaction equation

HRID 25564 reaction equation
[CH2:1]([O:8][C:9](=[O:18])[NH:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([OH:17])[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]Br.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:18])[NH:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([O:17][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][Br:19])[CH2:13][CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 123681,6-DibromohexaneHCID 14798Sodium HydroxideHCID 178523817HCID 178523817, compound

Product 1

HCID 178523821HCID 178523821, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

To 15.0 g (60 mmol) trans-4-Hydroxy-cyclohexylcarbamic acid benzyl ester suspended in 183 ml (1.2 mol, 20 eq) 1,6-Dibromohexane, 6.1 g (18 mmol, 0.3 eq) tetrabutyl-ammoniumhydrogensulfate and 183 ml 50% aqueous NaOH were added. The mixture was stirred at RT for 4 days, CH2Cl2 was added and the layers were separated. The inorganic layer was extracted with CH2Cl2, the combined organic layers were washed with brine and dried over Na2SO4. The excess of dibromide was removed in vacuo and the residue was purified by column chromatography on silica gel with hexane:EtOAc 1:1 as eluent yielding 3.4 g (14%) trans-[4-(6-Bromo-hexyloxy)-cyclohexyl]-carbamic acid benzyl ester as white solid, MS: 412 (MH30, 1Br) and 11.2 g (32%) trans-(6-Bromo-hexyl)-[4-(6-bromo-hexyloxy)-cyclohexyl]-carbamic acid benzyl ester as yellow oil, MS: 574 (MH+, 2Br).

Workup

  1. customthe layers were separated
  2. extractionThe inorganic layer was extracted with CH2Cl2
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. customThe excess of dibromide was removed in vacuo
  6. customthe residue was purified by column chromatography on silica gel with hexane:EtOAc 1:1 as eluent

Sources & evidence

ORD record
ord-c6114a35050143f9bbba24bbed9915b0
Source dataset
uspto-grants-2005_02
Patent number
US06858651B2

Reaction notes

Loading…