Benzoyl Peroxide → HCID 18348173, compound

HRID 2267968Notes

Reaction equation

HRID 2267968 reaction equation
[F:1][CH2:2][CH2:3][N:4]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[N:6]=[N:5]1.[Br:16]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[F:1][CH2:2][CH2:3][N:4]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][Br:16])=[CH:11][CH:10]=2)[N:6]=[N:5]1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 18348181HCID 18348181, compound

Product 1

HCID 18348173HCID 18348173, compoundYield 15.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Under a light source a stirred solution of 2.8 grams (0.013 mole) of 1-(2-fluoroethyl)-4-(4-methylphenyl)-1,2,3,5-(1H)-tetrazole, 2.4 grams (0.013 mole) of N-bromosuccinimide, and 0.19 gram (0.0008 mole) of benzoyl peroxide in 100 mL of carbon tetrachloride was heated to reflux. Once at reflux the reaction mixture was stirred for five hours. After this time the heat source was removed and the reaction mixture was stirred for about 18 hours. At the conclusion of this period the reaction mixture was filtered, and the filtrate was concentrated under reduced pressure, yielding 0.59 gram of 4-[1-(2-fluoroethyl)-1,2,3,5-(1H)-tetrazol-4-yl]benzyl bromide. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperatureOnce at reflux the reaction mixture
  2. customAfter this time the heat source was removed
  3. stirringthe reaction mixture was stirred for about 18 hours
  4. filtrationAt the conclusion of this period the reaction mixture was filtered
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7cc0d601b10641d9927ccf8cb976ded7
Source dataset
uspto-grants-2001_12
Patent number
USH0002007H1

Reaction notes

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