Water → 6-nitro-2,2-dimethyl-3-bromomethyl-2H-1-benzopyran

HRID 2399317Notes

Reaction equation

HRID 2399317 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C:11]([CH3:14])([CH3:13])[C:10]([CH3:15])=[CH:9][C:8]=2[CH:16]=1)([O-:3])=[O:2].[Br:17]N1C(=O)CCC1=O.O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C:11]([CH3:13])([CH3:14])[C:10]([CH2:15][Br:17])=[CH:9][C:8]=2[CH:16]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 157118816-nitro-2,2,3-trimethyl-2H-1-benzopyran

Product 1

HCID 193871046-nitro-2,2-dimethyl-3-bromomethyl-2H-1-benzopyranYield 90.5%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 6-nitro-2,2,3-trimethyl-2H-1-benzopyran (33.0 g, 0.151 mol) and benzoyl peroxide (0.020 g) in carbon tetrachloride (330 ml) were heated to 50° C. and N-bromo succinimide (26.8 g, 0.15 mol) was added. The mixture was heated at reflux for eighteen hours and then water and aqueous ferrous sulfate were added. The organic phase was separated and evaporated under reduced pressure, and the residue washed with pentane to give 40.45 g of 6-nitro-2,2-dimethyl-3-bromomethyl-2H-1-benzopyran, m.p. 107° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for eighteen hours
  3. customThe organic phase was separated
  4. customevaporated under reduced pressure
  5. washthe residue washed with pentane

Sources & evidence

ORD record
ord-bafd0644e2214aabaf2574812f9b89d8
Source dataset
uspto-grants-1995_09
Patent number
US05447943

Reaction notes

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