Carbon Tetrachloride → 4-Oxazolecarboxylic acid, 5-bromo-2-cyclopropyl-, methyl ester

HRID 1519238Notes

Reaction equation

HRID 1519238 reaction equation
[CH:1]1([C:4]2[O:5][CH:6]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[N:8]=2)[CH2:3][CH2:2]1.C1C(=O)N([Br:20])C(=O)C1.C(Cl)(Cl)(Cl)Cl>CCOC(C)=O>[Br:20][C:6]1[O:5][C:4]([CH:1]2[CH2:2][CH2:3]2)=[N:8][C:7]=1[C:9]([O:11][CH3:12])=[O:10]

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 67184N-bromobutanimideHCID 67452919HCID 67452919, compound

Product 1

HCID 674532884-Oxazolecarboxylic acid, 5-bromo-2-cyclopropyl-, methyl esterYield 58.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Into a 5000-mL 3-necked round-bottom flask were placed methyl 2-cyclopropyloxazole-4-carboxylate (140 g, 838.32 mmol, 1.00 equiv.), NBS (224 g, 1.26 mol, 1.50 equiv.), CCl4 (1400 mL) and BPO (20 g, 82.64 mmol, 0.10 equiv). The resulting solution was stirred overnight at room temperature, then it was diluted with 2000 mL of EtOAc. The solid was filtrated out. The filtrate was dried over anhydrous calcium chloride and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:50˜1:20). This resulted in 120 g (58% yield) of methyl 5-bromo-2-cyclopropyloxazole-4-carboxylate as a white solid.

Workup

  1. customInto a 5000-mL 3-necked round-bottom flask were placed
  2. filtrationThe solid was filtrated out
  3. dry with materialThe filtrate was dried over anhydrous calcium chloride
  4. concentrationconcentrated under vacuum
  5. washeluted with ethyl acetate/petroleum ether (1:50˜1:20)

Sources & evidence

ORD record
ord-5e2d479f7161406a9828c5c6b15fd79d
Source dataset
uspto-grants-2015_07
Patent number
US09073879B2

Reaction notes

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