5-Bromosalicylaldehyde → Methanone, (5-bromo-2-benzofuranyl)(5-methyl-2-phenyl-4-oxazolyl)-

HRID 963331

Reaction equation

HRID 963331 reaction equation
[Br:1][C:2]1[CH:9]=[C:6]([CH:7]=O)[C:5]([OH:10])=[CH:4][CH:3]=1.C[O-].[Na+].[C:14]1([C:20]2[O:21][C:22]([CH3:29])=[C:23]([C:25](=[O:28])[CH2:26]Br)[N:24]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C>[C:14]1([C:20]2[O:21][C:22]([CH3:29])=[C:23]([C:25]([C:26]3[O:10][C:5]4[CH:4]=[CH:3][C:2]([Br:1])=[CH:9][C:6]=4[CH:7]=3)=[O:28])[N:24]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 728635-BromosalicylaldehydeHCID 10942334Sodium Methoxide2×HCID 149136502-Bromo-1-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethan-1-one

Product 1

HCID 10500081Methanone, (5-bromo-2-benzofuranyl)(5-methyl-2-phenyl-4-oxazolyl)-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
780 °C

Procedure

To a slurry of 294 g of 5-bromosalicylaldehyde in 3 liters of dry ethanol was added 79.06 g of sodium methoxide and the mixture allowed to stir for 20 minutes. To the resulting yellow slurry was added 410 g of 2-phenyl-4-bromoacetyl-5-methyloxazole and the slurry heated to 780° C. for 2 hours. An additional 250 mg of sodium methoxide was added and heating continued overnight under a nitrogen atmosphere. The reaction was cooled and the solids filtered and washed with ethanol, 393 g, mp 212°-213° C.

Workup

  1. temperatureheating continued overnight under a nitrogen atmosphere
  2. temperatureThe reaction was cooled
  3. filtrationthe solids filtered
  4. washwashed with ethanol, 393 g, mp 212°-213° C.

Sources & evidence

ORD record
ord-e6494d0301f6494d96d173641848b4df
Source dataset
uspto-grants-1998_06
Patent number
US05763467

Linked notes

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