N-bromobutanimide → HCID 18381642, compound

HRID 2268896Notes

Reaction equation

HRID 2268896 reaction equation
[F:1][CH:2]([F:14])[O:3][C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][O:9][C:10]2=[O:13])=[CH:6][CH:5]=1.[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(Cl)(Cl)Cl>[Br:15][CH:8]1[C:7]2[C:11](=[CH:12][C:4]([O:3][CH:2]([F:1])[F:14])=[CH:5][CH:6]=2)[C:10](=[O:13])[O:9]1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 183816066-difluoromethoxy-3H-isobenzofuran-1-one

Product 1

HCID 18381642HCID 18381642, compoundYield 101.1%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6212ChloroformSolvent

Conditions

Temperature
76 °C

Procedure

A suspension of 6-difluoromethoxy-3H-isobenzofuran-1-one (1 g, 5 mmoles), prepared as described in example 94, in CCl4 (10 ml), under N2, was added with N-bromosuccinimide (0.91 g, 5.1 mmoles) and the mixture was heated at 76° C. A solution of α,α′-azaisobutyronitrile (0.01 g) in CHCl3 (1 ml) was slowly added. The mixture was refluxed for 1.5 hours, then cooled, filtered over celite and washed with CCl4. By drying, 1.41 g of the title compound were obtained as an oil (quantitative yield).

Workup

  1. customprepared
  2. temperatureThe mixture was refluxed for 1.5 hours
  3. temperaturecooled
  4. filtrationfiltered over celite
  5. washwashed with CCl4
  6. customBy drying

Sources & evidence

ORD record
ord-66632c421aec40a4a3b4c9e3c8f9979e
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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