1,3-Dibromopropane → HCID 57555329, compound

HRID 220812

Reaction equation

HRID 220812 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:4]([OH:17])[CH:3]=1.Br[CH2:19][CH2:20][CH2:21]Br.[OH-].[Na+]>C(#N)C.ClCCl.CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]([C:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:16])[CH2:19][CH2:20][CH2:21][O:17][C:4]=2[CH:3]=1

Participants

7

Reactant 3

HCID 80011,3-DibromopropaneHCID 14798Sodium HydroxideHCID 57555405N-(4-chloro-2-hydroxyphenyl)benzamide

Product 1

HCID 57555329HCID 57555329, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

N-(4-Chloro-2-hydroxy-phenyl)-benzamide from Example E25.1 (1.0 g, 4 mmol) was dissolved in acetonitrile (10 ml) and dichloromethane (15 ml). 1,3-Dibromopropane (3.26 g, 16 mmol), aliquat 336 (170 mg, 0.4 mmol) and sodium hydroxide (750 mg, 16 mmol) were added and the mixture was heated at 60° C. for 3 h. The solid was filtered off and the filtrate concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 30% EtOAc:70% hexane) to yield the title compound (783 mg, 83%).

Workup

  1. filtrationThe solid was filtered off
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe residue was purified by flash chromatography on silica gel (eluant; 30% EtOAc:70% hexane)

Sources & evidence

ORD record
ord-0074929384d8443cb58f7726401d9e14
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Linked notes

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