Water → HCID 86719126, compound

HRID 1844692Notes

Reaction equation

HRID 1844692 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[C:4]([Br:12])[CH:3]=1.[CH2:13]=[C:14](B(O)O)[CH3:15].C([O-])([O-])=O.[K+].[K+].O>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:12][C:4]1[CH:3]=[C:2]([C:14]([CH3:15])=[CH2:13])[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27611701,3-dibromo-5-tert-butylbenzeneHCID 10855372(Prop-1-en-2-yl)boronic acid

Product 1

HCID 86719126HCID 86719126, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1,3-dibromo-5-(tert-butyl)benzene (2.92 g, 10 mmol) in dioxane (20 mL) was added Pd(PPh3)4 (3.0 g, 2.6 mmol), prop-1-en-2-ylboronic acid (1.0 g, 12 mmol), K2CO3 (2.8 g, 20 mmol) and H2O (1 mL) under N2. The resulting mixture was stirred at 90° C. overnight, concentrated and purified by CC (hexane) to give compound P24a (2.5 g, 100%; 80% by GC/MS) as a liquid.

Workup

  1. concentrationconcentrated
  2. custompurified by CC (hexane)
  3. customto give compound P24a (2.5 g, 100%; 80% by GC/MS) as a liquid

Sources & evidence

ORD record
ord-c95b9c2812014e9d9c65f08e03e22a8f
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

Loading…