Sodium Azide → 1-(Azidomethyl)-3-[(5-bromo-2-chloro-3-fluorophenyl)oxy]-4-chloro-2-fluorobenzene

HRID 1874913Notes

Reaction equation

HRID 1874913 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([F:20])[C:5]([Cl:19])=[C:6]([O:8][C:9]2[C:14]([F:15])=[C:13]([CH2:16]Br)[CH:12]=[CH:11][C:10]=2[Cl:18])[CH:7]=1.[N-:21]=[N+:22]=[N-:23].[Na+]>CS(C)=O.CCOC(C)=O>[N:21]([CH2:16][C:13]1[CH:12]=[CH:11][C:10]([Cl:18])=[C:9]([O:8][C:6]2[CH:7]=[C:2]([Br:1])[CH:3]=[C:4]([F:20])[C:5]=2[Cl:19])[C:14]=1[F:15])=[N+:22]=[N-:23]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 866448922-[(5-Bromo-2-chloro-3-fluorophenyl)oxy]-4-(bromomethyl)-1-chloro-3-fluorobenzene

Product 1

HCID 866448931-(Azidomethyl)-3-[(5-bromo-2-chloro-3-fluorophenyl)oxy]-4-chloro-2-fluorobenzeneYield 90.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

2-[(5-bromo-2-chloro-3-fluorophenyl)oxy]-4-(bromomethyl)-1-chloro-3-fluorobenzene (10.04 g, 22.47 mmol) and sodium azide (1.461 g, 22.47 mmol) were combined in DMSO (50 mL) and stirred 3 days at 25° C. The reaction mixture was diluted with EtOAc, washed 4× with water, dried over MgSO4, filtered and concentrated to dryness to give 1-(azidomethyl)-3-[(5-bromo-2-chloro-3-fluorophenyl)oxy]-4-chloro-2-fluorobenzene (8.3 g, 20.29 mmol, 90% yield) as a clear oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.49-7.66 (m, 3H), 6.80 (s, 1H), 4.61 (s, 2H).

Workup

  1. washwashed 4× with water
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-550cfe6a78a847749864917ad7276725
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

Loading…