Water → 7-Fluoro-5-nitro-2,3-dihydrobenzo[b][1,4]dioxine

HRID 657013Notes

Reaction equation

HRID 657013 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([OH:9])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][CH2:21]Br.O>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[C:5]2[O:9][CH2:21][CH2:20][O:8][C:6]=2[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 688163705-Fluoro-3-nitrobenzene-1,2-diol

Product 1

HCID 688171507-Fluoro-5-nitro-2,3-dihydrobenzo[b][1,4]dioxineYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-fluoro-3-nitro-1,2-benzenediol (6.55 g, 37.9 mmol), anhydrous potassium carbonate (21 g, 151.6 mmol) and 1,2-dibromoethane (8.2 mL) in DMF (70 ml) was heated at 80° C. under argon for 5 h. The reaction was cooled to rt, water (200 ml) added and the aqueous phase extracted with ethyl acetate (3×200 ml). The organics were washed with brine, dried, filtered and evaporated to afford the desired compound (6.96 g, 93%).

Workup

  1. temperatureThe reaction was cooled to rt
  2. extractionthe aqueous phase extracted with ethyl acetate (3×200 ml)
  3. washThe organics were washed with brine
  4. customdried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-4416520aa71c46d1b012e729d37f4fa7
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

Loading…