N-bromobutanimide → HCID 58309376, compound

HRID 873496Notes

Reaction equation

HRID 873496 reaction equation
[S:1]1[C:5]2[C:6]3[S:11][CH:10]=[CH:9][C:7]=3[S:8][C:4]=2[CH:3]=[CH:2]1.C1C(=O)N([Br:19])C(=O)C1>>[Br:19][C:10]1[S:11][C:6]2[C:5]3[S:1][CH:2]=[CH:3][C:4]=3[S:8][C:7]=2[CH:9]=1

Participants

3

Reactant 2

HCID 67184N-bromobutanimideHCID 137985Dithieno(3,2-b:2',3'-d)thiophene

Product 1

HCID 58309376HCID 58309376, compound

Procedure

Compound 2 was synthesized as shown in Scheme 2. Under acid condition, dithieno[3,2-b:2′,3′-d]thiophene (Organic Syntheses, Vol. 83, p. 209 (2006)) was reacted with NBS affording 2-bromodithieno[3,2-b:2′,3′-d]thiophene 7, which underwent Suzuki cross-coupling reaction with boronic acid R1—B(OH)2 (J. Mater. Chem., 2010, 20, 2182-2189) to afford intermediate 8 in 71% yields. Finally 8 was converted to PhN—OFFT-TCN by reacting with n-BuLi and tetracyanoethylene at low temperature in 85% yield.

Sources & evidence

ORD record
ord-2007015ef45546cfa189195043e83460
Source dataset
uspto-grants-2015_03
Patent number
US08975419B2

Reaction notes

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