Hydrochloric Acid → HCID 12017659, compound

HRID 1006530Notes

Reaction equation

HRID 1006530 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[OH:13])=[O:4].Br[CH2:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C=O)C>[F:15][C:2]([F:1])([F:14])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[O:13][CH2:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=1)=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 256687Methyl 4-(bromomethyl)benzoateHCID 15688159HCID 15688159, compound

Product 1

HCID 12017659HCID 12017659, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-trifluoroacetylamino-5-chlorophenol (350 mg) and methyl 4-bromomethylbenzoate (435 mg) in DMF (3 ml), potassium carbonate (263 mg) was added at room temperature. The mixture was stirred for 1.5 hours at 60° C. After the termination of reaction, the reaction mixture was poured into diluted HCl and extracted with ethyl acetate. The organic layer was washed, dried over and concentrated under the reduced pressure. The residue was purified on silica gel column chromatography (AcOEt-benzene) to give the title compound (353 mg) having the following physical data.

Workup

  1. customAfter the termination of reaction
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed
  4. customdried over and
  5. concentrationconcentrated under the reduced pressure
  6. customThe residue was purified on silica gel column chromatography (AcOEt-benzene)

Sources & evidence

ORD record
ord-045232d067434e099c1d017f90ee9edd
Source dataset
uspto-grants-2004_09
Patent number
US06790866B2

Reaction notes

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