Sodium Azide → 1-(Azidomethyl)-4-fluoro-2-iodobenzene

HRID 1372327Notes

Reaction equation

Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[I:10].[N-:11]=[N+:12]=[N-:13].[Na+]>CN(C)C=O>[N:11]([CH2:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[I:10])=[N+:12]=[N-:13]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 1-(bromomethyl)-4-fluoro-2-iodobenzene (M. Protiva et al., Collect. Czech. Chem. Comm., 44, 1979, 2108–2123) (17.9 g, 56.8 mmol) in N,N-dimethylformamide (35 ml) was treated with sodium azide (5.0 g, 76.7 mmol) and the resulting mixture was heated to 50° C. for 4 h. The cooled mixture was filtered, the filtrate was concentrated in vacuo and the residue was chromatographed on silica gel (elution hexane) to give 15.7 g (97% yield) of the title azide as a clear oil. 1HNMR 400 MHz (DMSO-d6) δ (ppm): 4.53 (2H, s, CH2), 7.32 (1H, m, aromatic), 7.54 (1H, dd, J=6 Hz and J=8.6 Hz, aromatic), 7.83 (1H, dd, J=3 Hz and J=8 Hz, aromatic).

Workup

filtrationThe cooled mixture was filtered
concentrationthe filtrate was concentrated in vacuo
customthe residue was chromatographed on silica gel (elution hexane)

Sources & evidence

ORD record: ord-79f4954b890f4b89914bacbdbde03f52
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07157447B2

Reaction notes

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