4-Bromobenzamide → 4-bromo-N-(2,2-dichloro-1-hydroxybutyl)benzamide

HRID 1920086Notes

Reaction equation

HRID 1920086 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.[Cl:11][C:12]([Cl:17])([CH2:15][CH3:16])[CH:13]=[O:14]>Cl.O1CCOCC1>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:8][CH:13]([OH:14])[C:12]([Cl:17])([Cl:11])[CH2:15][CH3:16])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 696834-BromobenzamideHCID 112750512,2-Dichlorobutanal

Product 1

HCID 581495534-bromo-N-(2,2-dichloro-1-hydroxybutyl)benzamideYield 51%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 312751,4-DioxaneSolvent

Procedure

4-Bromobenzamide 118 (1.0 g, 4.85 mmol), 2,2-dichlorobutanal (2 mL) and HCl (3 drops) in dioxane (4 mL) were heated to 120° C. (bath temperature) for 18 hours. The mixture was concentrated, and absorbed onto silica gel. Chromatography (CH2Cl2) produced an off-white solid as 4-bromo-N-(2,2-dichloro-1-hydroxybutyl)benzamide 119 (0.84 g, 51%).

Workup

  1. concentrationThe mixture was concentrated
  2. customabsorbed onto silica gel

Sources & evidence

ORD record
ord-6facd840222d4cd5b72c0ce39c7c017e
Source dataset
uspto-grants-2012_05
Patent number
US08168795B2

Reaction notes

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