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

HRID 2367755Notes

Reaction equation

HRID 2367755 reaction equation
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

Participants

4

Reactant 3

HCID 27349353-Bromo-4-methylthiopheneHCID 50177412-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 178418339Butyllithium

Product 1

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

Procedure

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).

Sources & evidence

ORD record
ord-ece0ccfc902f4748965a953c70b97973
Source dataset
uspto-grants-2014_04
Patent number
US08697716B2

Reaction notes

Loading…