Diethyl Ether → N-(2,4-dihydroxyphenyl)-2,2,2-trifluoro-acetamide

HRID 18446Notes

Reaction equation

HRID 18446 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([O:9]C)[CH:6]=[CH:5][C:4]=1[NH:11][C:12](=[O:17])[C:13]([F:16])([F:15])[F:14].B(Br)(Br)Br.C([O-])(O)=O.[Na+].C(OCC)C>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[C:7]([OH:9])[CH:6]=[CH:5][C:4]=1[NH:11][C:12](=[O:17])[C:13]([F:14])([F:15])[F:16]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 5056099N-(2,4-dimethoxyphenyl)-2,2,2-trifluoroacetamide

Product 1

HCID 18454996N-(2,4-dihydroxyphenyl)-2,2,2-trifluoro-acetamideYield 83.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(2,4-dimethoxy phenyl)-2,2,2-trifluoro-acetamide (2.50 g; 10 mmol) in CH2Cl2 (20 mL) cooled to −10° C. was added 1 M BBr3 (CH2Cl2; 24 mL; 24 mmol) under N2 atmosphere. The mixture was allowed to warm to room temperature over 2 hours and poured onto H2O (150 mL). Saturated aqueous NaHCO3 (100 mL) and diethylether (100 mL) was added to dissolve any precipitated material. The organic layer was Isolated, washed with H2O (50 mL), dried (MgSO4), filtered and the eluate evaporated to dryness to yield 1.85 g (83%) of the desired compound as a greyish solid.

Workup

  1. additionpoured onto H2O (150 mL)
  2. dissolutionto dissolve any precipitated material
  3. customThe organic layer was Isolated
  4. washwashed with H2O (50 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe eluate evaporated to dryness

Sources & evidence

ORD record
ord-2d84f94ad95e48038928e9c8df4fb329
Source dataset
uspto-grants-2010_06
Patent number
US07741352B2

Reaction notes

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