Methanesulfonic Acid → HCID 23025824, compound

HRID 1437462Notes

Reaction equation

HRID 1437462 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.CS(O)(=O)=O.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:14]=1[OH:20].[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29](O)=O)=[CH:24][CH:23]=1.[OH-].[Na+]>>[Br:19][C:16]1[CH:17]=[CH:18][C:13]2[N:12]=[C:29]([CH2:28][C:25]3[CH:26]=[CH:27][C:22]([Cl:21])=[CH:23][CH:24]=3)[O:20][C:14]=2[CH:15]=1

Participants

6

Reactant 5

HCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 15880(4-Chlorophenyl)acetic acidHCID 24819Phosphorus pentachlorideHCID 143206052-Amino-5-bromophenol

Product 1

HCID 23025824HCID 23025824, compoundYield 71.2%

Conditions

Temperature
120 °C

Procedure

Phosphorus pentachloride (2.27 g) was added to methanesulfonic acid (8 ml), and the mixture was stirred at 120° C. for 1 hour. To the solution were added 2-amino-5-bromophenol (1.50 g) and 4-chlorophenylacetic acid (1.36 g) and the mixture was stirred at 100° C. for 1 hour. The mixture was poured onto ice, neutralized with 8 N sodium hydroxide and extracted with ethyl acetate-tetrahydrofuran (3:1, v/v). The organic layer was washed with water and dried over MgSO4. The solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography and the fraction eluted with ethyl acetate-hexane (1:4, v/v) was concentrated under reduced pressure. The resulting crystals were collected by filtration to obtain 6-bromo-2-(4-chlorobenzyl)benzoxazole (1.83 g, 71%).

Workup

  1. stirringthe mixture was stirred at 100° C. for 1 hour
  2. additionThe mixture was poured onto ice
  3. extractionextracted with ethyl acetate-tetrahydrofuran (3:1
  4. washThe organic layer was washed with water
  5. dry with materialdried over MgSO4
  6. distillationThe solvent was distilled off under reduced pressure
  7. washthe fraction eluted with ethyl acetate-hexane (1:4, v/v)
  8. concentrationwas concentrated under reduced pressure
  9. filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-b8d3043ab83f4c54a68fb11450ea06d7
Source dataset
uspto-grants-2009_11
Patent number
US07622479B2

Reaction notes

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