Ethyl 2-iodo-3-methylbenzoate → HCID 59314297, compound

HRID 1047901Notes

Reaction equation

HRID 1047901 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:6]=1I)[CH3:2].[CH3:14][C:15]([CH3:26])=[CH:16]B1OC(C)(C)C(C)(C)O1>CN(C=O)C.C([O-])(O)=O.[Na+]>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:6]=1[CH:14]=[C:15]([CH3:26])[CH3:16])[CH3:2]

Participants

5

Reactant 2

HCID 12140519Ethyl 2-iodo-3-methylbenzoateHCID 151484474,4,5,5-Tetramethyl-2-(2-methylprop-1-en-1-yl)-1,3,2-dioxaborolane

Product 1

HCID 59314297HCID 59314297, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
110 °C

Procedure

A suspension of the 2-iodo-3-methylbenzoic acid ethyl ester (289) (2.9 g-0.01 mol) and 2-methyl-1-propenylboronic acid pinacol ester (3.64 g-0.02 mol-2 eq) in dry DMF (50 mL) and saturated NaHCO3 (10 mL) is degassed for 10 minutes and then treated with tetrakis(triphenylphosphine)palladium(0) (400 mg). The mixture is stirred at 110° C. overnight. The reaction is cooled and the DMF removed in vacuo and the residue diluted with water (120 mL). The aqueous is filtered through hyflo and extracted with EtOAc (3×75 mL). The organic extracts are washed with water (2×50 mL) and brine (2×50 mL), and dried over MgSO4. The organic extracts are concentrated in vacuo and purified by flash chromatography (400 g silica gel, 5% EtOAc in heptane) to give the product as pale yellow oil (1.85 g, 85%).

Workup

  1. customis degassed for 10 minutes
  2. additiontreated with tetrakis(triphenylphosphine)palladium(0) (400 mg)
  3. temperatureThe reaction is cooled
  4. customthe DMF removed in vacuo
  5. additionthe residue diluted with water (120 mL)
  6. filtrationThe aqueous is filtered through hyflo
  7. extractionextracted with EtOAc (3×75 mL)
  8. washThe organic extracts are washed with water (2×50 mL) and brine (2×50 mL)
  9. dry with materialdried over MgSO4
  10. concentrationThe organic extracts are concentrated in vacuo
  11. custompurified by flash chromatography (400 g silica gel, 5% EtOAc in heptane)

Sources & evidence

ORD record
ord-2c4490287a224d58a2d3cce732176a0f
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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