1,2-Dibromoethane → 8-Nitro-2,3-dihydro-1,4-benzodioxine-6-carbaldehyde

HRID 401174Notes

Reaction equation

HRID 401174 reaction equation
O.O.[F-].[K+].[OH:5][C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[C:13]=1[OH:14])[CH:9]=[O:10].Br[CH2:19][CH2:20]Br>CN(C)C=O>[N+:15]([C:12]1[C:13]2[O:14][CH2:19][CH2:20][O:5][C:6]=2[CH:7]=[C:8]([CH:9]=[O:10])[CH:11]=1)([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 57489573,4-Dihydroxy-5-nitrobenzaldehydeHCID 23708904Potassium fluoride dihydrate

Product 1

HCID 218738188-Nitro-2,3-dihydro-1,4-benzodioxine-6-carbaldehydeYield 62.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

To a mixture of potassium fluoride dihydrate (2.573 g, 27.3 mmol), and 3,4-dihydroxy-5-nitrobenzaldehyde (500 mg, 2.73 mmol) in N,N-dimethylformamide (20 mL) was added 1,2-dibromoethane (3.8 mL, 43.7 mmol), and the mixture was heated at 130° C. for 17 h. The reaction mixture was quenched with water followed by a standard aqueous/EtOAc workup and purified by column chromatography on silica gel (petroleum ether/ethyl acetate=15:1) to give Intermediate 45 (350 mg, yield 62.1%).

Workup

  1. customThe reaction mixture was quenched with water
  2. custompurified by column chromatography on silica gel (petroleum ether/ethyl acetate=15:1)

Sources & evidence

ORD record
ord-f292cc54fc0f4747b02d5f38d3297170
Source dataset
uspto-grants-2014_06
Patent number
US08741915B2

Reaction notes

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