1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-Azidomethyl-2-iodo-benzene

HRID 1819420Notes

Reaction equation

HRID 1819420 reaction equation
[I:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]O.C1C=CC(P([N:24]=[N+:25]=[N-:26])(C2C=CC=CC=2)=O)=CC=1.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1.Cl.CCOCC>[N:24]([CH2:4][C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[I:1])=[N+:25]=[N-:26]

Participants

7

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 1076292-Iodobenzylic alcoholHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 116158581-Azidomethyl-2-iodo-benzeneYield 93%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2-iodobenzyl alcohol (6.0 g, 25.4 mmol) and DPPA (6.8 mL, 30.5 mmol) in toluene (65 mL) was added DBU (5.0 mL, 33.0 mmol). The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was then diluted with 3M HCl (60 mL) and ether (150 mL). The organic phase was separated and the aqueous phase was extracted with ether (×3). The combined organic extracts were washed with water (×2) and and then with brine. The solution was dried over anhydrous Na2SO4 and concentrated in vacuo. Silica gel column chromatography using 95:5 hexanes:EtOAc afforded 6.1 g (93%) of 1-azidomethyl-2-iodo-benzene.

Workup

  1. customThe organic phase was separated
  2. extractionthe aqueous phase was extracted with ether (×3)
  3. washThe combined organic extracts were washed with water (×2)
  4. dry with materialThe solution was dried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b60d8db06a62411cbcd2896b7183425d
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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