Azobisisobutyronitrile → 3-(4-Bromomethyl-benzooxazol-2-yl)-benzoic acid methyl ester

HRID 1694366Notes

Reaction equation

HRID 1694366 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[C:13]=3[N:14]=2)[CH:5]=1.[Br:21]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][Br:21])[C:13]=3[N:14]=2)[CH:5]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 672798453-(4-Methyl-benzooxazol-2-yl)-benzoic acid methyl ester

Product 1

HCID 672793503-(4-Bromomethyl-benzooxazol-2-yl)-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 3-(4-methyl-benzooxazol-2-yl)-benzoic acid methyl ester (1.2 mmol), N-bromo succinimide (1.5 mmol) and AIBN (0.3 mmol) in CCl4 are heated in microwave at 100° C. for 30 minutes (1 mL). The mixture is filtered and concentrated to yield the crude 3-(4-bromomethyl-benzooxazol-2-yl)-benzoic acid methyl ester. LC/MS (ES+): (M+) 346.1, 348.1, (M−Br) 266.1, 268.1.

Workup

  1. filtrationThe mixture is filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-1a7212b51dc14df085f73209174ecb48
Source dataset
uspto-grants-2012_04
Patent number
US08158662B2

Reaction notes

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