1,4-Dibromobutane → HCID 178484052, compound

HRID 967188Notes

Reaction equation

HRID 967188 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:21])[N:10]([CH2:12][C@H:13]2[CH2:18][CH2:17][C@H:16]([CH2:19][OH:20])[CH2:15][CH2:14]2)[CH3:11])=[CH:4][CH:3]=1.[Br:22][CH2:23][CH2:24][CH2:25][CH2:26]Br>ClCCl.[OH-].[Na+].S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9](=[O:21])[N:10]([CH2:12][C@H:13]2[CH2:18][CH2:17][C@H:16]([CH2:19][O:20][CH2:26][CH2:25][CH2:24][CH2:23][Br:22])[CH2:15][CH2:14]2)[CH3:11])=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 80561,4-DibromobutaneHCID 178484045HCID 178484045, compound

Product 1

HCID 178484052HCID 178484052, compound

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

In analogy to the method described in example 19.1, trans-(4-hydroxymethyl-cyclohexylmethyl)-methyl-carbamic acid 4-chloro-phenyl ester (example 5.3) was reacted with 1,4-dibromo-butane in dichloromethane and aqueous sodium hydroxide solution in the presence of tetrabutylammonium hydrogensulfate to yield trans-[4-(4-bromo-butoxymethyl)-cyclohexylmethyl]-methyl-carbamic acid 4-chloro-phenyl ester as colorless solid, MS: 446 (MH+, 1Cl, 1Br).

Sources & evidence

ORD record
ord-761886925d69412ea046865a91143941
Source dataset
uspto-grants-2005_10
Patent number
US06953806B2

Reaction notes

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