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Hydrogen Bromide → 6-[bromo(4-chlorophenyl)methyl]-1-methyl-1H-benzotriazole monohydrobromide

HRID 2248327
Notes
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Reaction equation

HRID 2248327 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:11]=[CH:12][C:13]3[N:17]=[N:16][N:15]([CH3:18])[C:14]=3[CH:19]=2)O)=[CH:4][CH:3]=1.[BrH:20]>C(O)(=O)C>[BrH:20].[Br:20][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:10]1[CH:11]=[CH:12][C:13]2[N:17]=[N:16][N:15]([CH3:18])[C:14]=2[CH:19]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 14990605alpha-(4-chlorophenyl)-1-methyl-1H-benzotriazole-6-methanol

Product 1

HCID 189243156-[bromo(4-chlorophenyl)methyl]-1-methyl-1H-benzotriazole monohydrobromideYield 76.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 245 parts of α-(4-chlorophenyl)-1-methyl-1H-benzotriazole-6-methanol and 1500 parts of a hydrobromic acid solution in acetic acid was stirred for 2.5 hours at 40° C. The reaction mixture was evaporated at 60° C. and the residue was stirred in dichloromethane. After cooling to 10° C., the precipitated product was filtered off and dried, yielding 285 parts (76.6%) of 6-[bromo(4-chlorophenyl)methyl]-1-methyl-1H-benzotriazole monohydrobromide (int. 130).

Workup

  1. customThe reaction mixture was evaporated at 60° C.
  2. stirringthe residue was stirred in dichloromethane
  3. temperatureAfter cooling to 10° C.
  4. filtrationthe precipitated product was filtered off
  5. customdried

Sources & evidence

ORD record
ord-fb8770758fa84b8d8af1e033b41bb8f4
Source dataset
uspto-grants-1991_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05039677

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes