Water → HCID 86719127, compound

HRID 1844694Notes

Reaction equation

HRID 1844694 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F: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:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=[C:2]([C:14]([CH3:15])=[CH2:13])[CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 20634891,3-Dibromo-5-(trifluoromethyl)benzeneHCID 10855372(Prop-1-en-2-yl)boronic acid

Product 1

HCID 86719127HCID 86719127, 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-(trifluoromethyl)benzene (3.03 g, 10 mmol) in dioxane (20 mL) was added Pd(PPh3)4 (300 mg, 0.26 mmol), prop-1-en-2-ylboronic acid (1.0 g, 12 mmol), K2CO3 (2.8 g, 20 mmol) and water (1 mL) under N2. The mixture was stirred at 90° C. overnight, concentrated and purified by CC (hexane) to afford compound P28a (1.9 g, 71%) as an oil.

Workup

  1. concentrationconcentrated
  2. custompurified by CC (hexane)
  3. customto afford compound P28a (1.9 g, 71%) as an oil

Sources & evidence

ORD record
ord-19a71ce63fca43b8a044e083dc6b40b5
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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