1,8-Diazabicyclo(5.4.0)undec-7-ene → Methyl 4-(azidomethyl)-2-chlorobenzoate

HRID 2270865Notes

Reaction equation

HRID 2270865 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([CH2:12]O)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C1(P([N:28]=[N+:29]=[N-:30])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>O1CCCC1>[N:28]([CH2:12][C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([Cl:1])[CH:11]=1)=[N+:29]=[N-:30]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 19780655Methyl 2-chloro-4-(hydroxymethyl)benzoate

Product 1

HCID 57461226Methyl 4-(azidomethyl)-2-chlorobenzoateYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-chloro-4-(hydroxymethyl)benzoic acid, methyl ester (11.09 g, 55.3 mmol), diphenylphosphoryl azide (22.58 g, 82.0 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (8.57 g, 56.3 mmol) in tetrahydrofuran was stirred overnight at room temperature. Silica gel was added and the solvent was evaporated. The residue was chromatographed (10% ethyl acetate/hexanes) to give 4-(azidomethyl)-2-chlorobenzoic acid, methyl ester (12.17 g, 98%) as a white solid.

Workup

  1. additionSilica gel was added
  2. customthe solvent was evaporated
  3. customThe residue was chromatographed (10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-cdc7067a73e640a9b4d9ea4b5c70f2e3
Source dataset
uspto-grants-2001_12
Patent number
US06331640B1

Reaction notes

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