8-BROMO-2,3-DIHYDRO-1,4-BENZODIOXINE-6-CARBALDEHYDE synthesis
- Product Name:8-BROMO-2,3-DIHYDRO-1,4-BENZODIOXINE-6-CARBALDEHYDE
- CAS Number:860003-88-9
- Molecular formula:C9H7BrO3
- Molecular Weight:243.05
16414-34-9
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106-93-4
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Yield:860003-88-9 99%
Reaction Conditions:
with potassium carbonate in DMF (N,N-dimethyl-formamide) at 100; for 20 h;
Steps:
36.2
To a solution of 3-bromo-4,5-dihydroxy-benzaldehyde (20.78 g, 95 mmol) in 480 ml DMF was added K2CO3 (52.95 g, 383 mmol) followed by 1,2-dibromoethane (8.7 ml, 101 mmol). The mixture was warmed to 100° C. After 18 additional 1,2 dibromoethane (1.0 mL) was added. After 2 h the mixture was poured into water and extracted with ethyl acetate. The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude solid was purified via flash chromatography (9:1 hexane/ethyl acetate) to give 8-bromo-2,3-dihydro-benzo[1,4]dioxine-6-carboxaldehyde (15.82 g, 99%) as a white solid.
References:
US2005/209260,2005,A1 Location in patent:Page/Page column 112
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2973-76-4
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860003-88-9
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