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

HRID 1263438Notes

Reaction equation

HRID 1263438 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]>>[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 513419766-(Bromomethyl)-1H-indazole hydrobromide

Procedure

A suspension of 1-acetyl-6-(acetoxymethyl)indazole (9.5 g, 41 mmol) (98) 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) δ4.85 (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-6ee5dc87528c4184b75bbc0b2bfa363e
Source dataset
uspto-grants-2003_04
Patent number
US06541467B1

Reaction notes

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