1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-(Azidomethyl)-2,3-difluoro-5-methoxybenzene

HRID 1527454Notes

Reaction equation

HRID 1527454 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([O:9][CH3:10])=[CH:4][C:3]=1[CH2:11]O.C1C=CC(P([N:27]=[N+:28]=[N-:29])(C2C=CC=CC=2)=O)=CC=1.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1.CCOC(C)=O>[N:27]([CH2:11][C:3]1[CH:4]=[C:5]([O:9][CH3:10])[CH:6]=[C:7]([F:8])[C:2]=1[F:1])=[N+:28]=[N-:29]

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 682836852,3-Difluoro-5-methoxybenzenemethanol

Product 1

HCID 866738621-(Azidomethyl)-2,3-difluoro-5-methoxybenzene

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2,3-difluoro-5-methoxy-phenyl)-methanol (715 mg, 4.11 mmol) in toluene (10 mL) was added DPPA (1.04 mL, 4.93 mmol) and DBU (0.805 mL, 5.34 mmol), followed by stirring at RT for 1 h. The reaction mixture was diluted with EtOAc, the organics were washed with diluted brine (20 mL), dried (Phase separator) and evaporated in vacuo. The residue was purified by flash column chromatography on silica gel (c-hexane/EtOAc 9:1) to afford the title compound as a colorless oil. TLC Rf (c-hexane/EtOAc 3:1)=0.55; MS (LC/MS): 208.0 [M+NH4]+; tR (HPLC conditions c): 5.46 min.

Workup

  1. washthe organics were washed with diluted brine (20 mL)
  2. customdried (Phase separator)
  3. customevaporated in vacuo
  4. customThe residue was purified by flash column chromatography on silica gel (c-hexane/EtOAc 9:1)

Sources & evidence

ORD record
ord-65a79888782a4a11a234b687c6a26fcf
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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