Sodium Azide → HCID 86599124, compound

HRID 2116013Notes

Reaction equation

CC1C=CC(S(O[CH2:12][CH:13]2[CH2:17][C:16]3[C:18]([F:30])=[C:19]([F:29])[CH:20]=[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[CH3:28])[C:15]=3[O:14]2)(=O)=O)=CC=1.[N-:31]=[N+:32]=[N-:33].[Na+]>>[F:30][C:18]1[C:16]2[CH2:17][CH:13]([CH2:12][N:31]=[N+:32]=[N-:33])[O:14][C:15]=2[C:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH3:28])=[CH:20][C:19]=1[F:29]

Participants

Reactant 2

HCID 33557Sodium Azide

HCID 86599123HCID 86599123, compound

Product 1

HCID 86599124HCID 86599124, compoundYield 90.1%

Procedure

Treatment of (±)-[4,5-difluoro-7-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate (1.3 g, 3.02 mmol) with sodium azide (0.983 g, 15.11 mmol) generally according to the procedure described for intermediate 98 gave 0.82 g (90%) of (±)-[4,5-difluoro-7-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl azide as a colorless oil. Rf=0.69 (silica, ethyl acetate:hexanes 1:4); 1H NMR (DMSO-d6) δH 7.25 (d, 2H); 7.14 (m, 3H); 5.06 (m, 1H); 3.67 (dd, 1H); 3.55 (dd, 1H); 3.46 (dd, 1H); 3.11 (dd, 1H); 2.15 (s, 3H).

Sources & evidence

ORD record: ord-385504912e404acb939c2f48601061cf
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07435837B2

Reaction notes

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