Sodium Hydroxide → HCID 66598539, compound

HRID 422371Notes

Reaction equation

HRID 422371 reaction equation
Br[CH2:2][CH2:3][C:4]#[C:5][Si:6]([CH3:9])([CH3:8])[CH3:7].[F:10][C:11]1[CH:19]=[CH:18][C:14]2[NH:15][N:16]=[N:17][C:13]=2[CH:12]=1.[OH-].[Na+]>>[F:10][C:11]1[CH:19]=[CH:18][C:14]2=[N:15][N:16]([CH2:2][CH2:3][C:4]#[C:5][Si:6]([CH3:9])([CH3:8])[CH3:7])[N:17]=[C:13]2[CH:12]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 642593silane, (4-bromo-1-butynyl)trimethyl-HCID 178505476HCID 178505476, compound

Product 1

HCID 66598539HCID 66598539, compoundYield 100%

Conditions

Temperature
100 °C

Procedure

(4-Bromo-but-1-ynyl)-trimethyl-silane (294 mg, 1.43 mmol) was added to a solution of 5-fluoro-1H-benzo[d][1,2,3]triazole (187 mg, 1.36 mmol) in a solution of NaOH (2N, 955 μL). The reaction mixture was heated at 100° C. for 14 hours, then it was cooled down and was extracted with DCM. The organic phase was washed with water, brine, dried over MgSO4, filtered and evaporated to yield 355 mg (1.36 mmol) 5-fluoro-2-(4-trimethylsilanyl-but-3-ynyl)-2H-benzo[d][1,2,3]triazole including the two others isomers.

Workup

  1. temperatureit was cooled down
  2. extractionwas extracted with DCM
  3. washThe organic phase was washed with water, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-9aa28227f2e94f57ae951d1ecbef0d0e
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

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