1,2-Dibromoethane → 1,4-Benzodioxin-6-carboxylic acid, 2,3-dihydro-5-nitro-, ethyl ester

HRID 1615671Notes

Reaction equation

HRID 1615671 reaction equation
[OH:1][C:2]1[C:3]([N+:14]([O-:16])=[O:15])=[C:4]([CH:10]=[CH:11][C:12]=1[OH:13])[C:5]([O:7][CH2:8][CH3:9])=[O:6].Br[CH2:18][CH2:19]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N+:14]([C:3]1[C:2]2[O:1][CH2:19][CH2:18][O:13][C:12]=2[CH:11]=[CH:10][C:4]=1[C:5]([O:7][CH2:8][CH3:9])=[O:6])([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 68089420HCID 68089420, compound

Product 1

HCID 680894081,4-Benzodioxin-6-carboxylic acid, 2,3-dihydro-5-nitro-, ethyl esterYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of ethyl 3,4-dihydroxy-2-nitrobenzoate (4.97 g, 21.9 mmol), 1,2-dibromoethane (6.70 g, 43.8 mmol), and potassium carbonate (6.04 g, 43.8 mmol) in DMF (100 mL) was stirred at 80° C. overnight. To the reaction mixture was added ice/water (100 mL), and the resulting mixture was extracted with EtOAc (200 mL×2). The extracts were combined and dried, and the solvent removed. The product was purified by silica gel column (10% v/v EtOAc in PE) to give ethyl 5-nitro-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxylate (4.30 g, 78% yield). ESI MS: m/z 254 [M+H]+.

Workup

  1. extractionthe resulting mixture was extracted with EtOAc (200 mL×2)
  2. customdried
  3. customthe solvent removed
  4. customThe product was purified by silica gel column (10% v/v EtOAc in PE)

Sources & evidence

ORD record
ord-db588bbf87d44bf5a74add439d8bb71f
Source dataset
uspto-grants-2014_07
Patent number
US08765760B2

Reaction notes

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