Dimethyl Sulfoxide → 2,3-Dimethylbutane-2,3-diol 2-(3-chloro-5-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 410501Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([Cl:11])[CH:3]=1.B1([B:21]2[O:25][C:24]([CH3:27])([CH3:26])[C:23]([CH3:29])([CH3:28])[O:22]2)[O:16][C:15]([CH3:18])([CH3:17])[C:14]([CH3:20])([CH3:19])[O:13]1.C([O-])(=O)C.[K+].CS(C)=O>C(OCC)(=O)C>[CH3:17][C:15]([OH:16])([C:14]([CH3:20])([OH:13])[CH3:19])[CH3:18].[Cl:11][C:4]1[CH:3]=[C:2]([B:21]2[O:22][C:23]([CH3:28])([CH3:29])[C:24]([CH3:26])([CH3:27])[O:25]2)[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A 20 mL microwave vial was charged with a stir bar, 1-bromo-3-chloro-5-nitrobenzene (1.182 g, 5.0 mmol), bis(pinacolato)diboron (1.397 mg, 5.5 mmol), PdCl2 (dppf)-dichloromethane adduct (204 mg, 0.25 mmol), potassium acetate (1.472 g, 15.0 mmol) and DMSO (10.00 mL). The vial was sealed and heated in a microwave at 120° C. for 30 minutes. The reaction mixture was diluted with ethyl acetate and washed twice with water, brine, and then dried over Na2SO4 to give 2,3-dimethylbutane-2,3-diol-2-(3-chloro-5-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1:1) (1.7 g, 85%) after filtration and solvent evaporation. The crude product mixture was used as is in the next reaction.

Workup

additionA 20 mL microwave vial was charged with a stir bar
customThe vial was sealed
washwashed twice with water, brine
dry with materialdried over Na2SO4

Sources & evidence

ORD record: ord-1ebfacbf5b4a48f4a91b287792f2465a
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759366B2

Reaction notes

Loading…