1,1-Dibromoethane → 5-Nitro-2,3-dihydro-1,4-benzodioxine

HRID 656910Notes

Reaction equation

HRID 656910 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[C:5]=1[OH:11])([O-:3])=[O:2].Br[CH:13](Br)[CH3:14].C([O-])([O-])=O.[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[N+:1]([C:4]1[C:5]2[O:11][CH2:14][CH2:13][O:10][C:6]=2[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 112011,1-DibromoethaneHCID 11430Potassium CarbonateHCID 4675622Nitrocatechol

Product 1

HCID 122313185-Nitro-2,3-dihydro-1,4-benzodioxineYield 93%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

3-Nitro-1,2-benzenediol (5 g; 32.26 mmol), dibromoethane (12.13 ml; 64.52 mmol), tetra(n-butyl)ammonium bromide (1.1 g; 32.26 mmol) and K2CO3 (13.35 g; 96.78 mmol) were stirred at reflux in toluene overnight. The reaction was then poured onto water (150 ml) and twice extracted with diethyl ether (2×150 ml). The combined organics were washed with water (100 ml) and brine (100 ml) then dried with MgSO4 and the solvents removed to afford the desired product (5.4 g; 93%).

Workup

  1. additionThe reaction was then poured onto water (150 ml)
  2. extractiontwice extracted with diethyl ether (2×150 ml)
  3. washThe combined organics were washed with water (100 ml) and brine (100 ml)
  4. dry with materialthen dried with MgSO4
  5. customthe solvents removed

Sources & evidence

ORD record
ord-acc3b6b6837141faae4d1b0c4d3defbc
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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