Thionyl Chloride → 6-Bromo-3-chloro-2-(4-trifluoromethylphenyl)-2H-indazole

HRID 270682Notes

Reaction equation

HRID 270682 reaction equation
[N:1]([C:4]1[CH:22]=[C:21]([Br:23])[CH:20]=[CH:19][C:5]=1[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)=O)=[N+]=[N-].O=S(Cl)[Cl:26]>>[Br:23][C:21]1[CH:20]=[CH:19][C:5]2[C:4]([CH:22]=1)=[N:1][N:8]([C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)[C:6]=2[Cl:26]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 860515492-Azido-4-bromo-N-(4-trifluoromethylphenyl)-benzamide

Product 1

HCID 692016176-Bromo-3-chloro-2-(4-trifluoromethylphenyl)-2H-indazoleYield 85%

Procedure

A solution of the product of Step 2 (3 g, 0.0078 mol) in SOCl2 (15 mL) was heated at reflux for 24 h. The mixture was then concentrated and the residue partitioned between ether (3×20 mL) and Na2CO3 solution (10 mL). The organic phase was separated, dried (MgSO4) and concentrated to give 2.5 g (85% yield) of product as a tan powder. 1H NMR (360 MHz, CDCl3): 7.25 (1H, d, J 8.9 Hz), 7.37 (1H, d, 8.9 Hz), 7.80-7.95 (5H, m).

Workup

  1. temperatureat reflux for 24 h
  2. concentrationThe mixture was then concentrated
  3. customthe residue partitioned between ether (3×20 mL) and Na2CO3 solution (10 mL)
  4. customThe organic phase was separated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-33609ee6604244e9b136f26b5ecde58c
Source dataset
uspto-grants-2008_11
Patent number
US07449585B2

Reaction notes

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