HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Azobisisobutyronitrile → 2-Bromomethyl-5-phenyl-benzoxazole

HRID 2120600
Notes
Print preview

Reaction equation

HRID 2120600 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:7][C:5]=2[N:6]=1.[Br:17]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:17][CH2:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)=[CH:7][C:5]=2[N:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6547Azobisisobutyronitrile2×HCID 67184N-bromobutanimideHCID 112786Benzoxazole, 2-methyl-5-phenyl-

Product 1

HCID 151337542-Bromomethyl-5-phenyl-benzoxazoleYield 32.3%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

2-Methyl-5-phenyl-benzoxazole 48 (1.05 g, 5.0 mmol), N-bromosuccinimide (89 mg, 5.0 mmol) and azodiisobutyronitrile (AIBN) (41 mg, 0.25 mmol) in 10 ml of CCl4 was heated to reflux. After 5 hrs an additional 50 mg AIBN were added and the mixture was refluxed overnight. The mixture was diluted, washed with water, dried and concentrated. The crude product was chromatographed to give about 465 mg 2-bromomethyl-5-phenyl-benzoxazole 49.

Workup

  1. temperaturethe mixture was refluxed overnight
  2. additionThe mixture was diluted
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe crude product was chromatographed

Sources & evidence

ORD record
ord-47ee6321853341c1bf74fe7372c3bb09
Source dataset
uspto-grants-2004_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06693098B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes