5-Chloro-2-methoxyaniline → HCID 76546138, compound

HRID 644458

Reaction equation

HRID 644458 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[O:13][CH3:14].[F:15][C:16]([F:30])([F:29])[C:17]1[CH:18]=[C:19]([CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=1)[CH:20]=[CH2:21]>O.[H+].[B-](F)(F)(F)F.CO.C(OCC)(=O)C>[Cl:12][C:10]1[CH:9]=[CH:8][C:7]([O:13][CH3:14])=[C:6]([CH:11]=1)[CH:21]=[CH:20][C:19]1[CH:22]=[C:23]([C:25]([F:26])([F:28])[F:27])[CH:24]=[C:17]([C:16]([F:15])([F:29])[F:30])[CH:18]=1

Participants

8

Reactant 3

HCID 667635-Chloro-2-methoxyanilineHCID 27732423,5-Bis(trifluoromethyl)styreneHCID 23668193Sodium Nitrite

Product 1

HCID 76546138HCID 76546138, compoundYield 34.7%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 28118Tetrafluoroboric acidSolvent

Conditions

Temperature
0 °C

Procedure

A solution of sodium nitrite (57 mg, 0.8 mmol) in water (1 mL) was added to a solution of 2-amino-4-chloroanisole (131 mg, 0.8 mmol) in 48% hydrogen tetrafluoroborate (0.3 mL) under ice cooling and argon atmosphere. After the mixture was stirred at 0° C. for 1 hour, a solution of 3,5-bis(trifluoromethyl)styrene (100 mg, 0.4 mmol) in methanol (3 mL) was added and the mixture was stirred at 50° C. for 1 hour. After the reaction mixture was cooled to room temperature, the residue obtained by evaporation of the solvent under reduced pressure was diluted with ethyl acetate. After the solution was washed successively with 2N hydrochloric acid, water and brine, dried over anhydrous sodium sulfate, the residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=5:1) to give the title compound (52.8 mg, 33.3%) as a white powder.

Workup

  1. stirringthe mixture was stirred at 50° C. for 1 hour
  2. temperatureAfter the reaction mixture was cooled to room temperature
  3. customthe residue obtained by evaporation of the solvent under reduced pressure
  4. washAfter the solution was washed successively with 2N hydrochloric acid, water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe residue obtained by evaporation of the solvent under reduced pressure
  7. customwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-84c38d26b4db498692231614c5f962f7
Source dataset
uspto-grants-2010_04
Patent number
US07700655B2

Linked notes

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