Sodium Azide → (2'-Azidomethyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester

HRID 563612Notes

Reaction equation

HRID 563612 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[CH2:23]Br)[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1.[N-:26]=[N+:27]=[N-:28].[Na+]>CS(C)=O.CCOC(C)=O.O>[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[CH2:23][N:26]=[N+:27]=[N-:28])[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 66606639(2'-Bromomethyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester

Product 1

HCID 86651117(2'-Azidomethyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To (2′-bromomethyl-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester (0.867 g, 2.08 mmol) in DMSO (9 mL) was added sodium azide (0.175 g, 2.49 mmol), and the reaction was stirred at 60° C. for 4 hours. The mixture was cooled to room temperature and diluted with EtOAc and H2O. The aqueous layer was extracted with EtOAc, and the combined organic layers were washed with H2O, then brine, and dried over MgSO4, filtered, and concentrated to give the title compound.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washthe combined organic layers were washed with H2O
  4. dry with materialbrine, and dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-60f4f8eababb4a17846886c887ab5d1f
Source dataset
uspto-grants-2011_11
Patent number
US08067445B2

Reaction notes

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