Sodium Hydroxide → 5-Bromo-2-[2-fluoro-4-(methylsulfonyl)phenyl]benzo[d]oxazole

HRID 710088Notes

Reaction equation

HRID 710088 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[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+]>CCOC(C)=O.O>[Br:8][C:6]1[CH:5]=[CH:4][C:3]2[O:9][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])=[N:1][C:2]=2[CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 3518402-Amino-4-BromophenolHCID 283559322-Fluoro-4-(methylsulphonyl)benzoic acid

Product 1

HCID 712573645-Bromo-2-[2-fluoro-4-(methylsulfonyl)phenyl]benzo[d]oxazoleYield 80.5%

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Conditions

Temperature
195 °C

Procedure

2-Amino-4-bromophenol (1.77 g, 9.4 mmol) and 2-fluoro-4-(methylsulfonyl)benzoic acid (2 g, 9.4 mmol) were dissolved in polyposphoric acid (60 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 was purified on combiflash with a gradient mixture of EtOAc and Petether (33:67) to obtain the titled compound (2.8 g) as an off-white solid.

Workup

  1. customReaction mixture
  2. temperaturecooled to rt
  3. customfollowed by evaporation of EtOAc
  4. customafforded the crude
  5. customCrude was purified on combiflash with a gradient mixture of EtOAc and Petether (33:67)

Sources & evidence

ORD record
ord-b6ccfc43630f4ef9bd8166b587ac03d4
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

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