126120-85-2

Usage

Chemical Properties

Solid

InChI:InChI=1/C8H4F2O4/c9-8(10)13-5-3-1-2-4(7(11)12)6(5)14-8/h1-3H,(H,11,12)

Upstream product

• 1583-59-1 2,2-difluoro-1,3-benzodioxole 
• 124-38-9 carbon dioxide 

Downstream Products

• 531508-32-4 methyl 2,2-difluoro-1,3-benzodioxole-4-carboxylate 
• 1637586-83-4 C₂₀H₁₉F₂N₃O₅ 
• 1404097-46-6 4-(1-(2,2-difluorobenzo[d][1,3]dioxole-4-carbonyl)piperidin-4-yloxy)-3-fluorobenzaldehyde 
• 162506-37-8 2,2-difluoro-7-methylsulphenyl-1,3-benzodioxol-4-oyl chloride 
• 143096-86-0 2,2-difluoro-1,3-benzodioxole-4-carbonyl chloride 
• 531508-46-0 (2,2-difluorobenzo[d][1,3]dioxol-4-yl)methanamine 
• 106876-54-4 2,2-difluoro-1,3-benzodioxol-4-ylamine 
• 161886-18-6 2,2-difluoro-1,3-benzodioxol-4-carbonitrile 

Relevant academic research and scientific papers

2-, 3-, and 4-(Trifluoromethoxy)phenyllithiums: Versatile intermediates offering access to a variety of new organofluorine compounds

Consecutive treatment of (trifluoromethoxy)benzene with sec-butyllithium and electrophilic reagents affords previously inaccessible ortho-substituted derivatives in generally excellent yields. 2-(Trifluoromethoxy)phenyllithium acts as the key intermediate. The 3- and 4-isomers can readily be generated from the corresponding 3- and 4-bromo precursors by halogen-metal interconversion with butyllithium or tertbutyllithium. Upon trapping of the 2-, 3- and 4-(trifluoromethoxy)phenyllithiums with 11 different electrophiles the expected products were formed in generally high yields. Only the attempted nucleophilic addition of 2-(trifluoromethoxy)phenyllithium to oxirane did not succeed. This failure is tentatively attributed to a lowering of the nucleophilicity by fluorine-lithium interactions. Conformationally restricted analogs - i.e., 2,2-difluoro-1,3-benzodioxol-4-phenyllithium and its 5-fluoro- and 5-bromo-substituted congeners - did indeed react smoothly with oxirane, affording the adducts in ordinary yields.

Process for the preparation of substituted difluorobenzo-1,3-dioxoles

The reaction of 2,2-difluorobenzo-1,3-dioxole with (a) an alkali metal or an alkali metal compound and then (b) a compound R1 -Z1 l in which Z1 is a leaving group, or with an aldehyde produces compounds of formula I STR1 wherein R1 l is --OH, --SH, --CHO, --CN, --COOH, --B(OH)2, --COX, with X being Cl or Br, or is --COOR2, --SiR32 or --B(OR2)2, with R2 being a C1 -C12 alcohol moiety without the hydroxy group, wherein R1 is further --Cn H2n COOR2, with n being an integer from 1 to 4, or linear or branched C1 -C12 hydroxyalkyl which is unsubstituted or is substituted by --F, --CN, C1 -C6 alkoxy, phenyl, fluorophenyl, C1 -C4 alkoxy-phenyl, C1 -C4 alkylthio-phenyl, C1 -C4 alkyl-phenyl, C1 -C4 fluoroalkyl-phenyl, nitrophenyl or by cyanophenyl, or wherein R1 is a benzyl alcohol which is unsubstituted or is substituted by F, C1 -C4 alkoxy, C1 -C4 alkylthio, C1 -C4 alkyl, C1 -C4 fluoroalkyl, nitro or by cyano, or is C1 -C12 acyl, or wherein R 1 is a radical of formula II STR2 wherein R5 is --CN, --CF3, --COOR2, --CO--NHR2 or --CONR22, R3 and R4 are a direct bond or each is H, or R3 is H and R4 independently has the meanings of R5, or R3 and R4 together are --CH2 --NR6 --CH2 --, --CH2 --NR6 --CO-- or --CO--NR6 --CO-- wherein R6 is the radical of a removable protecting group, or wherein further R1 is a radical of formula III STR3 Insecticides or fungicides can be prepared from the compounds of formula I. 3-(2,2-difluorobenzodioxol-4-yl)-4-cyanopyrrole can be prepared by reacting 4-metallo-2,2-difluorobenzodioxole (III) with an unsaturated nitrile and then with a sulfonylmethyl isocyanide in a one-pot process. The compounds III are novel intermediates.