Water → 2-[4-(Trifluoromethyl)phenyl]-4-(4-bromophenyl)-5-methyloxazole

HRID 724449Notes

Reaction equation

HRID 724449 reaction equation
[N:1]1C=CC=CC=1.[Br:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15](=NO)[CH3:16])=[CH:10][CH:9]=1.C1(C)C=CC=CC=1.[F:26][C:27]([F:39])([F:38])[C:28]1[CH:33]=[CH:32][C:31]([CH2:34]C(Cl)=O)=[CH:30][CH:29]=1.[OH2:40]>>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[N:1]=[C:34]([C:31]3[CH:32]=[CH:33][C:28]([C:27]([F:39])([F:38])[F:26])=[CH:29][CH:30]=3)[O:40][C:15]=2[CH3:16])=[CH:12][CH:13]=1

Participants

6

Reactant 5

HCID 962WaterHCID 1049PyridineHCID 1140TolueneHCID 148109432-(4-(Trifluoromethyl)phenyl)acetyl chlorideHCID 71333301HCID 71333301, compound

Product 1

HCID 106912782-[4-(Trifluoromethyl)phenyl]-4-(4-bromophenyl)-5-methyloxazoleYield 43%

Procedure

Pyridine (3.55 mL, 43.86 mmol) was added into a mixture of 1-(4-bromo-phenyl)-propanone oxime (10.0 g, 43.86 mmol) and toluene (20 mL). The reaction mixture was stirred for 30 minutes, and then 4-trifluoromethyl-phenyl acetyl chloride (16.27 mL, 109.6 mmol) was added dropwise. The new mixture was stirred at 100° C. for 24 hours, and then w as poured into water and extracted with ethyl acetate. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography on silica gel (hexanes/EtAOc 40:1) gave a white solid (7.3 g, 43% yield): mp 82.84° C.; MS m/e 381 (M+);

Workup

  1. stirringThe new mixture was stirred at 100° C. for 24 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic extracts were dried over MgSO4
  4. customEvaporation and purification by flash chromatography on silica gel (hexanes/EtAOc 40:1)

Sources & evidence

ORD record
ord-5527bd4b1ba4483fbbca6003eefd4cf9
Source dataset
uspto-grants-2006_11
Patent number
US07141672B2

Reaction notes

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