7-CHLORO-1,3-BENZODIOXOLE-5-CARBALDEHYDE synthesis

7synthesis methods

Product Name:7-CHLORO-1,3-BENZODIOXOLE-5-CARBALDEHYDE
CAS Number:88525-51-3
Molecular formula:C8H5ClO3
Molecular Weight:184.58

75-27-4
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34098-18-5 Synthesis

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7-CHLORO-1,3-BENZODIOXOLE-5-CARBALDEHYDE

88525-51-3
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$75.00/50mg

Yield:88525-51-3 70%

Reaction Conditions:

with caesium carbonate in N,N-dimethyl-formamide at 60;

Steps:

6.b; 18 7-Chlorobenzo[d][1,3]dioxole-5-carbaldehyde

To a solution of 3-chloro-4,5-dihydroxybenzaldehyde (8.0 g, 46 mmol) and BrClCH2 (23.9 g, 185 mmol) in dry DMF (100 mL) was added Cs2CO3 (25 g, 190 mmol).
The mixture was stirred at 60° C. overnight and was then poured into water.
The resulting mixture was extracted with EtOAc (50 mL*3).
The combined extracts were washed with brine (100 mL), dried over Na2SO4 and concentrated under reduced pressure to afford 7-chlorobenzo[d][1,3]dioxole-5-carbaldehyde (6.0 g, 70%).
1H NMR (400 MHz, CDCl3) δ 9.74 (s, 1H), 7.42 (d, J=0.4 Hz, 1H), 7.26 (d, J=3.6 Hz, 1H), 6.15 (s, 2H)

References:

US2015/231142,2015,A1 Location in patent:Paragraph 1133; 1585