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

HRID 655998Notes

Reaction equation

HRID 655998 reaction equation
P([N:17]=[N+:18]=[N-:19])(=O)(OC1C=CC=CC=1)OC1C=CC=CC=1.N12CCCN=C1CCCCC2.[Br:31][C:32]1[C:33]([O:40][CH3:41])=[C:34]([CH2:38]O)[CH:35]=[CH:36][CH:37]=1>C1(C)C=CC=CC=1>[N:17]([CH2:38][C:34]1[CH:35]=[CH:36][CH:37]=[C:32]([Br:31])[C:33]=1[O:40][CH3:41])=[N+:18]=[N-:19]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 123414Diphenylphosphoryl azideHCID 177503163-Bromo-2-methoxybenzenemethanol

Product 1

HCID 597786811-(Azidomethyl)-3-bromo-2-methoxybenzene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6.00 g of diphenyl phosphorazidate and 4.1 g of 1,8-diazabicyclo[5.4.0]undec-7-ene were added to 4.0 g of 3-bromo-2-methoxy-phenyl-methanol 6 in 100 mL of toluene at 0° C. The mixture was stirred at room temperature overnight. The reaction mixture was quenched with aqueous ammonium chloride. The aqueous layer was extracted with ethyl acetate/THF. The pooled organic extracts were washed with brine and dried over magnesium sulfate. The mixture was filtered. The solvents were removed under vacuum. The residue was purified by chromatography on silica gel to give 1-azidomethyl-3-bromo-2-methoxy-benzene 7.

Workup

  1. customThe reaction mixture was quenched with aqueous ammonium chloride
  2. extractionThe aqueous layer was extracted with ethyl acetate/THF
  3. washThe pooled organic extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe mixture was filtered
  6. customThe solvents were removed under vacuum
  7. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-f764ca0408c54365972521280286b1c4
Source dataset
uspto-grants-2011_12
Patent number
US08071636B2

Reaction notes

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