Ethyl Acetate → Benzene, 2-(azidomethyl)-4-chloro-1-(trifluoromethoxy)-

HRID 1819401Notes

Reaction equation

HRID 1819401 reaction equation
C1CCN2C(=NCCC2)CC1.[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([O:21][C:22]([F:25])([F:24])[F:23])=[C:17]([CH2:19]O)[CH:18]=1.C1C=CC(P([N:40]=[N+:41]=[N-:42])(C2C=CC=CC=2)=O)=CC=1.CCOC(C)=O>C1(C)C=CC=CC=1>[N:40]([CH2:19][C:17]1[CH:18]=[C:13]([Cl:12])[CH:14]=[CH:15][C:16]=1[O:21][C:22]([F:25])([F:24])[F:23])=[N+:41]=[N-:42]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 573686245-Chloro-2-(trifluoromethoxy)benzylalcohol

Product 1

HCID 57885582Benzene, 2-(azidomethyl)-4-chloro-1-(trifluoromethoxy)-Yield 65%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

DBU (1.0 mL, 6.7 mmol) was added to a solution of (5-chloro-2-trifluoromethoxy-phenyl)-methanol (1.2 g, 5.3 mmol) and DPPA (1.4 mL, 6.4 mmol) in toluene (30 mL) at room temperature. After 3 h, the reaction was concentrated in vacuo to yield an yellow oil. Silica gel column chromatography using 95:5 hexanes:EtOAc yielded 0.86g (65%) of 2-azidomethyl-4-chloro-1-trifluoromethoxy-benzene as a colorless oil.

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. customto yield an yellow oil

Sources & evidence

ORD record
ord-73d834bc3f804d31abaee3c938bf8af7
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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