1-Bromo-3-chloropropane → 1-(3-chloropropyl)-6-fluoro-1H-benzotriazole

HRID 1482620Notes

Reaction equation

HRID 1482620 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[N:8][NH:7][C:6]=2[CH:10]=1.[OH-].[Na+].[Cl:13][CH2:14][CH2:15][CH2:16]Br>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:13][CH2:14][CH2:15][CH2:16][N:7]1[C:6]2[CH:10]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[N:9]=[N:8]1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 14798Sodium HydroxideHCID 178505478HCID 178505478, compound

Product 1

HCID 1183868471-(3-chloropropyl)-6-fluoro-1H-benzotriazoleYield 32.3%

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Conditions

Temperature
60 °C

Procedure

6-fluoro-1H-benzotriazole (13.7 g, 0.10 mol) is dissolved into 100 ml of 30% wt. sodium hydroxide, 3-chlorobromopropane (31.4 g, 0.10 mol), tetrabutyl ammonium bromide (0.8 g) are added, and mixed for 5 min. The reaction solution is gradually heated to 60° C., stirred for reaction for 2 hours. Post treatment was performed based on common method one for synthesis. The solution was separated and purified by HPLC to produce 6.9 g of 1-(3-chloropropyl)-6-fluoro-1H-benzotriazole, with a yield of 32.3%.

Workup

  1. additionare added
  2. additionmixed for 5 min
  3. customPost treatment was performed based on common method one for synthesis
  4. customThe solution was separated
  5. custompurified by HPLC

Sources & evidence

ORD record
ord-b11b650ab3454197b4f4aa2642d90efd
Source dataset
uspto-grants-2016_08
Patent number
US09415047B2

Reaction notes

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