Sodium Hydroxide → HCID 71257300, compound

HRID 710089Notes

Reaction equation

HRID 710089 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[C:4]([F:9])[C:3]=1[OH:10].[F:11][C:12]1[CH:20]=[C:19]([S:21]([CH3:24])(=[O:23])=[O:22])[CH:18]=[CH:17][C:13]=1[C:14](O)=O.[OH-].[Na+]>CCOC(C)=O.O>[Br:8][C:6]1[CH:5]=[C:4]([F:9])[C:3]2[O:10][C:14]([C:13]3[CH:17]=[CH:18][C:19]([S:21]([CH3:24])(=[O:22])=[O:23])=[CH:20][C:12]=3[F:11])=[N:1][C:2]=2[CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 27376372-Amino-4-bromo-6-fluorophenolHCID 283559322-Fluoro-4-(methylsulphonyl)benzoic acid

Product 1

HCID 71257300HCID 71257300, compound

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Conditions

Temperature
195 °C

Procedure

2-Amino-4-bromo-6-fluorophenol (2.6 g, 9.7 mmol) and 2-fluoro-4-(methylsulfonyl)benzoic acid (2.1 g, 9.7 mmol) were dissolved in polyposphoric acid (63.5 g). This mixture was heated at 195° C. for three and half hours. Reaction mixture cooled to rt and diluted with ice water (100 ml). Aqueous layer basified with sodium hydroxide pellets to pH 9. Work up (EtOAc/H2O) followed by evaporation of EtOAc afforded the crude. Crude (3.1 g) was used in the next step without further purification.

Workup

  1. customReaction mixture
  2. temperaturecooled to rt
  3. customfollowed by evaporation of EtOAc
  4. customafforded the crude
  5. customCrude (3.1 g) was used in the next step without further purification

Sources & evidence

ORD record
ord-92f53721d5b14bfabd6dd4f27220cb63
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

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