1,4-Dibromobutane → HCID 178485980, compound

HRID 25543

Reaction equation

HRID 25543 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([O:9][C:10](=[O:20])[N:11]([C@H:13]2[CH2:18][CH2:17][C@H:16]([OH:19])[CH2:15][CH2:14]2)[CH3:12])[CH:5]=[CH:6][C:7]=1[F:8].[OH-].[Na+].[Br:23][CH2:24][CH2:25][CH2:26][CH2:27]Br>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[F:1][C:2]1[CH:3]=[C:4]([O:9][C:10](=[O:20])[N:11]([C@H:13]2[CH2:18][CH2:17][C@H:16]([O:19][CH2:27][CH2:26][CH2:25][CH2:24][Br:23])[CH2:15][CH2:14]2)[CH3:12])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 14798Sodium HydroxideHCID 178485979HCID 178485979, compound

Product 1

HCID 178485980HCID 178485980, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 94433Tetrabutylammonium hydrogen sulfateCatalyst

Procedure

A solution of 11.6 g (containing 31 mmol) of crude trans-(4-Hydroxy-cyclohexyl)-methyl-carbamic acid 3,4-difluoro-phenyl ester in 110 ml of 1,4-dibromobutane was treated with 3.16 g (9.3 mmol) tetrabutylammonium hydrogen sulfate and 200 ml of aqueous 50% NaOH and stirred for 2.5 days at RT. The reaction was extracted (CH2Cl2 2×). The organic phase was dried over Na2SO4, evaporated and purified by flash silica gel column (first with hexane to remove the dibromobutane and then hexane/EtOAc 1:1) to yield 4.06 g (31%) of trans-[4-(4-bromo-butoxy)-cyclohexyl]-methyl-carbamic acid 3,4-difluoro-phenyl ester, MS: 420 (M, 1Br).

Workup

  1. extractionThe reaction was extracted (CH2Cl2 2×)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customevaporated
  4. custompurified by flash silica gel column (first with hexane
  5. customto remove the dibromobutane

Sources & evidence

ORD record
ord-8862db1a54a94de0908797be4694ab12
Source dataset
uspto-grants-2005_02
Patent number
US06858651B2

Linked notes

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