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

HRID 561251Notes

Reaction equation

HRID 561251 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-7e35a3e2ba2e41e188a3492ce7ecf64c
Source dataset
uspto-grants-2011_11
Patent number
US08063231B2

Reaction notes

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