HCID 11048255, compound → HCID 10870788, compound

HRID 634634Notes

Reaction equation

HRID 634634 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:28]C)=[C:6]([C:8]([C:10]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:11]=2[NH:20]C(OC(C)(C)C)=O)=[O:9])[CH:7]=1>C(Cl)Cl.B(Br)(Br)Br>[NH2:20][C:11]1[CH:12]=[CH:13][C:14]([C:16]([F:17])([F:18])[F:19])=[CH:15][C:10]=1[C:8]([C:6]1[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[OH:28])=[O:9]

Participants

4

Reactant 1

HCID 11048255HCID 11048255, compound

Product 1

HCID 10870788HCID 10870788, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 25134Boron tribromideSolvent

Procedure

To a cold solution (−78° C.) of N-[2-[(5-chloro-2-methoxyphenyl) carbonyl]-4-(trifluoromethyl) phenyl]aminocarboxylic acid, 1,1-dimethylethyl ester prepared in Example 1, Step A (7.0 g, 21.2 mmol) in methylene chloride (60 mL), 1.0 M BBr3 solution in methylene chloride (46.7 mL, 46.7 mmol) was added dropwise. The resultant red solution was allowed to warm to room temperature and stirred overnight. The reaction mixture was quenched with saturated NaHCO3 solution. The organic layer was separated and washed with water, brine and then dried (MgSO4). Evaporation of the solvent gave a yellow-reddish solid which was recrystallized from CH2Cl2/hexanes to afford the title compound as a yellow solid (6.58 g, 98%).

Workup

  1. customThe reaction mixture was quenched with saturated NaHCO3 solution
  2. customThe organic layer was separated
  3. washwashed with water, brine
  4. dry with materialdried (MgSO4)
  5. customEvaporation of the solvent
  6. customgave a yellow-reddish solid which
  7. customwas recrystallized from CH2Cl2/hexanes

Sources & evidence

ORD record
ord-4f57afbf0a9f484cb120912a896087ee
Source dataset
uspto-grants-2001_02
Patent number
US06184231B2

Reaction notes

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