Triethylamine → 4-Methyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid tert-butyl ester

HRID 723024Notes

Reaction equation

HRID 723024 reaction equation
[C:1]([O:5][C:6](=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9](C)[C:8]=1I)([CH3:4])([CH3:3])[CH3:2].[CH2:16](N(CC)CC)C.[CH3:23][C:24]1([CH3:31])[C:28]([CH3:30])([CH3:29])[O:27][BH:26][O:25]1>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:5][C:6](=[O:15])[C:7]1[CH:12]=[CH:11][C:10]([CH3:16])=[CH:9][C:8]=1[B:26]1[O:27][C:28]([CH3:30])([CH3:29])[C:24]([CH3:31])([CH3:23])[O:25]1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneHCID 58415860Tert-butyl 2-iodo-3-methylbenzoate

Product 1

HCID 695868564-Methyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid tert-butyl esterYield 64%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

The procedure used in Example 3: step b was followed using 2-iodo-3-methyl-benzoic acid tert-butyl ester ((Example 4: step a) 960 mg, 3 mmol), PdCl2(PPh3)2 (126 mg, 0.18 mmol), triethylamine (1.25 mL, 9 mmol), and 4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (660 μL, 4.5 mmol) in dioxane (12 mL) at a reaction temperature of 80° C. Analogous aqueous workup and purification by SiO2 flash chromatography yielded the title compound (618 mg, 64%). 1H-NMR (CDCl3): δ 7.67 (m, 1H), 7.25 (m, 2H), 2.43 (s, 3H), 1.57 (m, 9H), 1.44 (m, 12H).

Workup

  1. customat a reaction temperature of 80° C
  2. customAnalogous aqueous workup and purification by SiO2 flash chromatography

Sources & evidence

ORD record
ord-2d561b94f50548079239f3ba271426d3
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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