Sodium Hydroxide → HCID 71554884, compound

HRID 1777405Notes

Reaction equation

HRID 1777405 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:4]=[C:5]([NH:13][C:14](=[O:25])[C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[C:17]([CH3:22])[C:16]=2[O:23]C)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.B(Br)(Br)Br.[OH-].[Na+]>C(Cl)Cl>[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([NH:13][C:14](=[O:25])[C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[C:17]([CH3:22])[C:16]=2[OH:23])[CH:4]=[C:3]([C:2]([F:1])([F:26])[F:27])[CH:8]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 90312925HCID 90312925, compound

Product 1

HCID 71554884HCID 71554884, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(3,5-bis(trifluoromethyl)phenyl)-5-chloro-2-methoxy-3-methylbenzamide (1 g, 2.43 mmol) prepared in step 1 was dissolved in CH2Cl2 (15 ml), to which boron tribromide (3.54 ml, 12.15 mmol) was added at −70° C., followed by stirring at room temperature for 3 hours. The mixture was dropped in 20 ml of cold ice water, followed by stirring for 30 more minutes. The mixture was cooled down at room temperature, to which aqueous sodium hydroxide was dropped 6˜7 drops. Extraction was performed with dichloromethane. The organic extract was mixed, dried over MgSO4, and concentrated under reduced pressure, followed by chromatography (ethylacetate:hexane=1:5) to give 930 mg of the target compound (yield: 96%).

Workup

  1. additionwas added at −70° C.
  2. stirringby stirring for 30 more minutes
  3. additionwas dropped 6˜7 drops
  4. extractionExtraction
  5. extractionThe organic extract
  6. additionwas mixed
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4ab3bc0c9cbf41878dd74c961cdb5298
Source dataset
uspto-grants-2016_02
Patent number
US09266872B2

Reaction notes

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