Sodium Azide → 3-{[3-(Azidomethyl)-6-chloro-2-fluorophenyl]oxy}-5-bromobenzonitrile

HRID 1874886Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[C:16]([Cl:17])=[CH:15][CH:14]=[C:13]([CH2:18]Br)[C:12]=2[F:20])[CH:9]=1)[C:5]#[N:6].[N-:21]=[N+:22]=[N-:23].[Na+]>CS(C)=O.CCOC(C)=O>[N:21]([CH2:18][C:13]1[C:12]([F:20])=[C:11]([O:10][C:8]2[CH:7]=[C:4]([CH:3]=[C:2]([Br:1])[CH:9]=2)[C:5]#[N:6])[C:16]([Cl:17])=[CH:15][CH:14]=1)=[N+:22]=[N-:23]

Participants

Conditions

Temperature: 25 °C

Procedure

3-bromo-5-{[3-(bromomethyl)-6-chloro-2-fluorophenyl]oxy}benzonitrile (2.25 g, 5.36 mmol) and sodium azide (0.349 g, 5.36 mmol) were combined in DMSO (10 mL) and stirred overnight at 25° C. The reaction mixture was diluted with EtOAc, washed 4× with water, dried over MgSO4, filtered and concentrated to dryness to give 3-{[3-(azidomethyl)-6-chloro-2-fluorophenyl]oxy}-5-bromobenzonitrile (2.04 g, 5.35 mmol, 100% yield) as a clear oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.93 (t, 1H), 7.48-7.63 (m, 4H), 4.60 (s, 2H).

Workup

washwashed 4× with water
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-104c6383d2a446b1be80c55ade4de050
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304419B2

Reaction notes

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