1,4-Dibromobutane → HCID 11486256, compound

HRID 380344Notes

Reaction equation

HRID 380344 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([S:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1.[Br:19][CH2:20][CH2:21][CH2:22][CH2:23]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)CC(=O)C>[Br:19][CH2:20][CH2:21][CH2:22][CH2:23][O:1][C:2]1[CH:3]=[C:4]([S:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 11470958HCID 11470958, compound

Product 1

HCID 11486256HCID 11486256, compound

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A stirred mixture of methyl 4-(3-hydroxyphenylsulfanyl)benzoate (13.0 g, 50.0 mmol) and 1,4-dibromobutane (21.0 g, 0.1 mol), anhydrous potassium carbonate (16.0 g) and 4-methylpentane-2-one (150 ml) was refluxed for 13 h. The hot mixture was filtered, the filtrate was evaporated to dryness and the partially crystalline residue was dissolved in a mixture of dichloromethane-petroleum ether (1:1) and then purified by column chromatography on silica gel using the same solvent mixture. The title ester was obtained as the main fraction (15.2 g, 76.9%), m.p. 43-45° C. For C16H19BrO3S (395.3) calculated: 54.69% C, 4.84% H, 20.22% Br, 8.11% S; found: 54.71% C, 4.80% H, 20.09% Br, 8.07% S.

Workup

  1. temperaturewas refluxed for 13 h
  2. filtrationThe hot mixture was filtered
  3. customthe filtrate was evaporated to dryness
  4. dissolutionthe partially crystalline residue was dissolved in a mixture of dichloromethane-petroleum ether (1:1)
  5. custompurified by column chromatography on silica gel using the same solvent mixture

Sources & evidence

ORD record
ord-90200de930d14d79aebf598e2448d33d
Source dataset
uspto-grants-2001_10
Patent number
US06303612B1

Reaction notes

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