Hydrogen Bromide → 6-(Bromomethyl)-1H-indazole

HRID 1634150Notes

Reaction equation

HRID 1634150 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH2:13]OC(=O)C)[CH:11]=2)[CH:6]=[N:5]1)(=O)C.[BrH:18]>>[Br:18][CH2:13][C:10]1[CH:11]=[C:12]2[C:7]([CH:6]=[N:5][NH:4]2)=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 186161831-Acetyl-6-(acetoxymethyl)indazole

Product 1

HCID 186161916-(Bromomethyl)-1H-indazole

Procedure

A suspension of 1-acetyl-6-(acetoxymethyl)indazole (9.5 g, 41 mmol) (4-4) in aqueous hydrobromic acid (48% aqueous solution, 20 mL, 177 mmol) was stirred at room temperature for 46 hours. The solid was collected on a Buchner funnel and dried under vacuum for 12 hours. The filtrate was stirred at room temperature for additional 24 hours and more solid was collected. After drying under vacuum, title compound was obtained as a yellow solid (10.0 g, 84%) which was used as such without further purification. MS (electrospray) 211 (M+1 for 79Br), 213 (M+1 for 81Br); 1H N MR (CDCl3) δ 4.85 (s, 2H), 7.65 (d, 1H, J=8.4 Hz), 7.78 (d, 1H, J 8.4 Hz), 8.05 (s, 1H), 8.10 (s, 1H).

Workup

  1. customThe solid was collected on a Buchner funnel
  2. customdried under vacuum for 12 hours
  3. stirringThe filtrate was stirred at room temperature for additional 24 hours
  4. custommore solid was collected
  5. customAfter drying under vacuum

Sources & evidence

ORD record
ord-5a09fa46bf384e24a3eb8d01a49122fc
Source dataset
uspto-grants-2003_01
Patent number
US06506760B1

Reaction notes

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