Dichloromethane → HCID 86687921, compound

HRID 2401460Notes

Reaction equation

HRID 2401460 reaction equation
[CH3:1][O:2][C:3]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([CH3:16])[CH:4]=1.C1C(=O)N([Br:24])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C.C(Cl)Cl>CC#N.O>[Br:24][CH2:16][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 6547Azobisisobutyronitrile4×HCID 67184N-bromobutanimide2×HCID 86687920HCID 86687920, compound

Product 1

HCID 86687921HCID 86687921, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of methyl 4-methoxy-2-methyl-5-nitrobenzoate (994 mg, 4.41 mmol) and NBS (943 mg, 5.3 mmol) in MeCN (20 mL) was degassed and then AIBN (15 mg, 0.09 mmol) was added. The mixture was heated to 70° C. for 18 h. Further AIBN (15 mg, 0.09 mmol) was added and the mixture was heated to 70° C. for 24 h. Further AIBN (15 mg, 0.09 mmol) and NBS (300 mg, 1.7 mmol) were added and the mixture heated to 70° C. for 24 h. Further AIBN (15 mg, 0.09 mmol) was added and the mixture was heated to 70° C. for 24 h. DCM (50 mL) and water (50 mL) were added and the organic phase was passed through a hydrophobic frit. The solvent was removed in vacuo to give crude methyl 2-(bromomethyl)-4-methoxy-5-nitrobenzoate that was used directly in the next reaction without any purification.

Workup

  1. customwas degassed
  2. temperaturethe mixture was heated to 70° C. for 24 h
  3. temperaturethe mixture heated to 70° C. for 24 h
  4. temperaturethe mixture was heated to 70° C. for 24 h
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-987cd44eeb464fe1a80753de8ffd3dd2
Source dataset
uspto-grants-2014_08
Patent number
US08796296B2

Reaction notes

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