1-Bromo-2-Chloroethane → 3'-[(2-Bromoethyl)oxy]-4-biphenylcarboxamide

HRID 471790Notes

Reaction equation

HRID 471790 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([NH2:16])=[O:15])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[Br:17][CH2:18][CH2:19][Cl:20].C(=O)([O-])[O-].[K+].[K+]>C(O)C.O.C(OCC)(=O)C>[Cl:20][CH2:19][CH2:18][O:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([NH2:16])=[O:15])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[Br:17][CH2:18][CH2:19][O:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([NH2:16])=[O:15])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 582763863'-Hydroxy-[1,1'-biphenyl]-4-carboxamide

Product 2

HCID 582762623'-[(2-Bromoethyl)oxy]-4-biphenylcarboxamideHCID 582763523'-[(2-Chloroethyl)oxy]-4-biphenylcarboxamide

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Into three separate microwave vials was distributed equally a mixture of 3′-hydroxy-4-biphenylcarboxamide (Intermediate A-1-1) (1.0 g, 0.005 mol), 1-bromo-2-chloroethane (2.8 g, 0.02 mol) and potassium carbonate (2.8 g, 0.02 mol) in ethanol (2.2 mL) and water (1.8 mL) was placed in a microwave at 150° C. until the reaction was complete as determined by LC/MS. The contents of the vials were combined and diluted with ethyl acetate and water. The aqueous phase was extracted with ethyl acetate. The combined organic phase was dried (Na2SO4), filtered and concentrated in vacuo to give 3′-[(2-chloroethyl)oxy]-4-biphenylcarboxamide and 3′-[(2-bromoethyl)oxy]-4-biphenylcarboxamide as an off-white solid. LC/MS indicates that this product is a mixture of the chloroethoxy (M+H) 276, 2.34 min. (LC/MS method A) and the bromoethoxy (M+H) 320, tR 2.42 min. in a ratio of ˜81/19% respectively. This product was used without further purification.

Workup

  1. customInto three separate microwave vials
  2. customwas placed in a microwave at 150° C. until the reaction
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. dry with materialThe combined organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d65534616d0249ba92534e89944578f2
Source dataset
uspto-grants-2014_01
Patent number
US08633175B2

Reaction notes

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