4,7-Di(thiophen-2-yl)benzo(c)(1,2,5)thiadiazole → Tributyltin bromide

HRID 1351715

反応式

HRID 1351715 の反応式
[Br:1]C1SC(C2C3C(=NSN=3)C(C3SC(Br)=CC=3)=CC=2)=CC=1.S1C=CC=C1C1C2C(=NSN=2)C(C2SC=CC=2)=CC=1.BrC1C2C(=NSN=2)C(Br)=CC=1.[CH2:52]([Sn:56](CCCC)([CH2:62][CH2:63][CH2:64][CH3:65])[C:57]1S[CH:59]=[CH:60][CH:61]=1)[CH2:53][CH2:54][CH3:55]>>[CH2:52]([Sn:56]([Br:1])([CH2:62][CH2:63][CH2:64][CH3:65])[CH2:57][CH2:61][CH2:60][CH3:59])[CH2:53][CH2:54][CH3:55]

参加物

5

反応物 4

HCID 3962944,7-Di(thiophen-2-yl)benzo(c)(1,2,5)thiadiazoleHCID 6263614,7-Dibromo-2,1,3-benzothiadiazoleHCID 27793732-(Tri-n-butylstannyl)thiophene2 回HCID 223816544,7-Bis(2-bromo-5-thienyl)-2,1,3-benzothiadiazole

生成物 1

HCID 305767Tributyltin bromide

実験手順

The 4,7-bis(5-bromothien-2-yl)-2,1,3-benzothiadiazole is traditionally prepared from 4,7-bis(thien-2-yl)-2,1,3-benzothiadiazole, which in turn is prepared by the Stille coupling reaction of 4,7-dibromo-2,1,3-benzothiadiazole with tributyl(thien-2-yl)stannane as described by Kitamura et al., Chem. Mater., Vol. 8, 1996, pp. 570–578. Unfortunately, tributyl(thien-2-yl) stannane is a highly toxic and costly material that produces a toxic by-product tributyltin bromide. The process is further disadvantaged because the subsequent bromination reaction is carried out in a mixture of N-bromosuccinimide, chloroform, and acetic acid, which requires numerous crystallizations of the product to obtain a suitably pure material in the subsequent copolymerization reaction.

出典と根拠

ORDレコード
ord-d1ae17b4609e465e8768ae7b3a53334d
出典データセット
uspto-grants-2007_05
特許番号
US07217824B2

関連ノート

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