2-Bromo-1-(4-fluorophenyl)ethan-1-one → HCID 57433608, compound

HRID 1783806Notes

Reaction equation

HRID 1783806 reaction equation
[NH2:1][C:2]1[O:3][CH:4]=[CH:5][N:6]=1.[Br:7][CH2:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)=[O:10]>C(#N)C.C1COCC1>[BrH:7].[F:17][C:14]1[CH:15]=[CH:16][C:11]([C:9](=[O:10])[CH2:8][N:6]2[CH:5]=[CH:4][O:3][C:2]2=[NH:1])=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-oneHCID 5585212-Aminooxazole

Product 1

HCID 57433608HCID 57433608, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-amino-oxazole (14.9 g, 0.179 mol) in acetonitrile (100 ml) was slowly added over a period of 20 minutes to a solution of 2-bromo-1-(4-fluorophenyl)ethanone (57.6 g, 0.36 mol) in THF (150 ml). The reaction mixture was stirred at room temperature for 24 hrs then cooled to 0° C. A precipitate formed and was filtered off. The solid was washed with three portions of 30 ml of cold acetonitrile and dried at 50° C. under vacuum, yielding 38.75 g (72%) of an off-white solid. M.p.=218-221° C.; 300 MHz 1H NMR (DMSO-d6) δ: 9.80 (br. s, 1H), 8.16-8.11 (m, 2H), 8.00 (s, 1H), 7.62 (s, 1H), 7.52-7.46 (m, 2H), 5.80 (s, 2H); LCMS: 221 [M+H]. Calc. for C11H9N2O2F.1.05HBr.0.14ACN: C, 43.58; H, 3.39; N, 9.64. Found C, 43.63; H, 3.38; N, 9.65.

Workup

  1. temperaturethen cooled to 0° C
  2. customA precipitate formed
  3. filtrationwas filtered off
  4. washThe solid was washed with three portions of 30 ml of cold acetonitrile
  5. customdried at 50° C. under vacuum

Sources & evidence

ORD record
ord-8799287d4d7444818b0c364e181e36be
Source dataset
uspto-grants-2009_03
Patent number
US07501430B2

Reaction notes

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