Potassium Carbonate → 2-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzylsulfanyl]-benzofuran

HRID 29488Notes

Reaction equation

[S:1]1[CH:5]=[C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[OH:12])N=N1.Br[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([B:21]2[O:25][C:24]([CH3:27])([CH3:26])[C:23]([CH3:29])([CH3:28])[O:22]2)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:26][C:24]1([CH3:27])[C:23]([CH3:28])([CH3:29])[O:22][B:21]([C:18]2[CH:17]=[CH:16][C:15]([CH2:14][S:1][C:5]3[O:12][C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=4[CH:4]=3)=[CH:20][CH:19]=2)[O:25]1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 2-[1,2,3]thiadiazol-4-yl-phenol (241 mg, 1.35 mmol, 1 eq, prepared according to M. A. Abramov, W. Dehaen, B. D'hooge, M. L. Petrov, S. Smeets, S. Toppet and M. Voets Tetrahedron, 2000, 56, 3933-3940), 2-(4-bromomethyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (406 mg, 1.37 mmol, 1 eq), and potassium carbonate (396 mg, 2.87 mmol, 1.9 eq) was dissolved in 8 mL of acetonitrile and heated to 90° C. under a nitrogen atmosphere. After the reaction was complete as monitored by TLC, the mixture was filtered and the solvent removed in vacuo. The resulting crude material was chromatographed on silica gel eluting with 20% ethyl acetate/hexane to give 2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzylsulfanyl]-benzofuran (198 mg) in 40% yield. 1H NMR (400 MHz, CDCl3) δ ppm 1.3 (s, 12 H) 4.1 (s, 2 H) 6.6 (d, J=1.0 Hz, 1 H) 7.2 (m, 4 H) 7.4 (d, J=7.8 Hz, 2 H) 7.7 (d, J=8.1 Hz, 2 H).

Workup

customprepared
filtrationthe mixture was filtered
customthe solvent removed in vacuo
customThe resulting crude material was chromatographed on silica gel eluting with 20% ethyl acetate/hexane

Sources & evidence

ORD record: ord-f6f991bdf3ee4b609bded8a21fc71da6
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07420001B2

Reaction notes

Loading…