Sodium Hydroxide → HCID 71257341, compound

HRID 710097Notes

Reaction equation

HRID 710097 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[OH:9].[F:10][C:11]1[CH:19]=[C:18]([S:20]([CH3:23])(=[O:22])=[O:21])[CH:17]=[CH:16][C:12]=1[C:13](O)=O.[OH-].[Na+]>>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[N:1]=[C:13]([C:12]3[CH:16]=[CH:17][C:18]([S:20]([CH3:23])(=[O:21])=[O:22])=[CH:19][C:11]=3[F:10])[O:9][C:3]=2[CH:4]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 143206052-Amino-5-bromophenolHCID 283559322-Fluoro-4-(methylsulphonyl)benzoic acid

Product 1

HCID 71257341HCID 71257341, compoundYield 13.2%

Conditions

Temperature
195 °C

Procedure

2-amino-5-bromophenol (1.72 g, 9.2 mmol) and 2-fluoro-4-(methylsulfonyl)benzoic acid (2 g, 9.2 mmol) were dissolved in polyposphoric acid (30 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. Solid that formed was filtered and dried to obtain the crude. Crude was purified by combiflash using a gradient mixture of EtOAc and Petether (1:3) as eluent to afford the titled compound (450 mg) as a dark brown solid.

Workup

  1. customReaction mixture
  2. temperaturecooled to rt
  3. customSolid that formed
  4. filtrationwas filtered
  5. customdried
  6. customto obtain the crude
  7. customCrude was purified by combiflash
  8. additiona gradient mixture of EtOAc and Petether (1:3) as eluent

Sources & evidence

ORD record
ord-7d032d3f32394817af7e648037b7de09
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

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