3-Bromo-4-methylthiophene → 4,4,5,5-Tetramethyl-2-(2-methylthiophen-3-yl)-1,3,2-dioxaborolane

反応式

Br[C:2]1[C:6](C)=[CH:5][S:4][CH:3]=1.[Li][CH2:9]CCC.C(O[B:17]1[O:21][C:20]([CH3:23])([CH3:22])[C:19]([CH3:25])([CH3:24])[O:18]1)(C)C>>[CH3:24][C:19]1([CH3:25])[C:20]([CH3:23])([CH3:22])[O:21][B:17]([C:6]2[CH:2]=[CH:3][S:4][C:5]=2[CH3:9])[O:18]1

参加物

反応物 3

HCID 27349353-Bromo-4-methylthiophene

HCID 50177412-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HCID 178418339Butyllithium

生成物 1

HCID 455881264,4,5,5-Tetramethyl-2-(2-methylthiophen-3-yl)-1,3,2-dioxaborolane収率 26%

実験手順

Using a procedure similar to Example 4, step (b), 3-bromo-4-methylthiophene (571 mg, 3.2 mmol) was treated with n-BuLi (1.41 mL, 2.5M/hexanes) and then allowed to react with 2-isopropoxy-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (775 μL, 3.8 mmol) to afford 189 mg (26%) of the title compound as a colorless oil. 1H-NMR (CDCl3; 400 MHz): δ 1.32 (s, 12H), 2.42 (s, 3H), 6.90-6.91 (m, 1H), 7.84 (d, 1H, J=2.9 Hz).

出典と根拠

ORDレコード: ord-4812dd7edc4245269ec0d47f572c91fd
出典データセット: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08933091B2

反応ノート

読み込み中…

参加物