Trifluoroacetic acid → HCID 86708461, compound

HRID 1430786Notes

Reaction equation

HRID 1430786 reaction equation
[C:1]([O:5][C:6]([N:8](C(OC(C)(C)C)=O)[C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([Br:20])[C:18]=1[Cl:19])[C:12]([O:14][CH3:15])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:20][C:17]1[CH:16]=[C:11]([CH:10]=[C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:18]=1[Cl:19])[C:12]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86708462HCID 86708462, compound

Product 1

HCID 86708461HCID 86708461, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methyl 3-(bis(tert-butoxycarbonyl)amino)-5-bromo-4-chlorobenzoate (3.06 g, 6.58 mmol) was dissolved in a solution of TFA (1.015 ml, 13.17 mmol) in CH2Cl2 (32.9 ml). The reaction was stirred at rt for 45 min, and then sat. NaHCO3 solution was added. The reaction mixture was diluted with a little more CH2Cl2 and washed 2× with sat. NaHCO3 to remove any residual TFA. The organic layer was dried over Na2SO4, filtered, and concentrated to provide methyl 3-bromo-5-(tert-butoxycarbonylamino)-4-chlorobenzoate (2.33 g) as a cream solid.

Workup

  1. washwashed 2× with sat. NaHCO3
  2. customto remove any residual TFA
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-436f47ffbf444165abb687bb0c8dad37
Source dataset
uspto-grants-2015_01
Patent number
US08940736B2

Reaction notes

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