N-bromobutanimide → HCID 15895947, compound

HRID 397850Notes

Reaction equation

HRID 397850 reaction equation
[F:1][C:2]1[C:11]2[O:10][CH2:9][CH:8]([C:12]#[N:13])[O:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.C1C(=O)N([Br:21])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[F:1][C:2]1[C:11]2[O:10][CH2:9][C:8]([Br:21])([C:12]#[N:13])[O:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 230013505-Fluoro-1,4-benzodioxane-2-carbonitrile

Product 1

HCID 15895947HCID 15895947, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
70 °C

Procedure

A solution containing 6.44 g of the nitrile obtained in Stage 2 (36 mmol), 6.40 g of NBS (36 mmol, 1 eq.), and 100 mg of benzoyl peroxide in 200 ml of CCl4 is heated at 70° C. for 48 hours. The mixture is allowed to cool to room temperature. The reaction mixture is then filtered. The solid is washed with CCl4 and the mother liquors are evaporated to dryness. 9.3 g of an orange-yellow oil are isolated (quantitative yield).

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe reaction mixture is then filtered
  3. washThe solid is washed with CCl4
  4. customthe mother liquors are evaporated to dryness

Sources & evidence

ORD record
ord-9a90c428121445fb8387f17aa25f2f9f
Source dataset
uspto-grants-2003_08
Patent number
US06610725B1

Reaction notes

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