N-bromobutanimide → Methyl 2-(4-(bromomethyl)phenyl)-5-fluorobenzo[d]oxazole-7-carboxylate

HRID 415206Notes

Reaction equation

HRID 415206 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:18]([O:20][CH3:21])=[O:19])[C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=3)=[N:7][C:6]=2[CH:17]=1.C1C(=O)N([Br:29])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:29][CH2:16][C:13]1[CH:12]=[CH:11][C:10]([C:8]2[O:9][C:5]3[C:4]([C:18]([O:20][CH3:21])=[O:19])=[CH:3][C:2]([F:1])=[CH:17][C:6]=3[N:7]=2)=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 66620785HCID 66620785, compound

Product 1

HCID 66621057Methyl 2-(4-(bromomethyl)phenyl)-5-fluorobenzo[d]oxazole-7-carboxylateYield 65.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To methyl 5-fluoro-2-p-tolylbenzo[d]oxazole-7-carboxylate (420 mg, 1.47 mmol) in CCl4 (5 mL) was added NBS (262 mg, 1.47 mmol) and BPO (69 mg, 0.735 mmol), the resulting mixture was heated to reflux for 24 hr; then the solvent was evaporated and the residue was purified by silica gel chromatography (petroleum ether:ethyl acetate=100:1-50:1) to obtain methyl 2-(4-(bromomethyl)phenyl)-5-fluorobenzo[d]oxazole-7-carboxylate as a white solid (350 mg, yield 65%). LC-MS (ESI) m/z 264 [M+1]+.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 24 hr
  3. customthen the solvent was evaporated
  4. customthe residue was purified by silica gel chromatography (petroleum ether:ethyl acetate=100:1-50:1)

Sources & evidence

ORD record
ord-ffe7380a6f6c4f6182247155688e181b
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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