Tetrabutylammonium borohydride → HCID 67070116, compound

HRID 1924445Notes

Reaction equation

HRID 1924445 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]([NH:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1)=O.[BH4-].C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)Cl>[F:1][C:2]([F:16])([F:17])[CH2:3][NH:5][C:6]1[CH:7]=[CH:8][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 169536Tetrabutylammonium borohydrideHCID 786481HCID 786481, compound

Product 1

HCID 67070116HCID 67070116, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

step c—A vial was charged with 122 (1.0 g, 4.05 mmol) and DCM (15 mL) then tetrabutylammonium borohydride was added. The vial was capped and heated overnight in an oil bath at 50° C. The reaction mixture was cooled to RT and the DCM was evaporated. HOAc was added dropwise until H2 evolution ceased. The solvents were evaporated and toluene was added. The mixture was made basic with dilute NaHCO3, extracted with EtOAc, dried (MgSO4), filtered and evaporated. The resulting solid was recrystallized from hexane to afford 0.349 g of methyl 4-(2,2,2-trifluoro-ethylamino)-benzoate (124)

Workup

  1. customThe vial was capped
  2. temperatureThe reaction mixture was cooled to RT
  3. customthe DCM was evaporated
  4. additionHOAc was added dropwise until H2 evolution
  5. customThe solvents were evaporated
  6. additiontoluene was added
  7. extractionextracted with EtOAc
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customevaporated
  11. customThe resulting solid was recrystallized from hexane

Sources & evidence

ORD record
ord-82b526c065fe430eb245d7812cede589
Source dataset
uspto-grants-2012_05
Patent number
US08178547B2

Reaction notes

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