Iodoethane → Ethyl 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate

HRID 2364618Notes

Reaction equation

HRID 2364618 reaction equation
[CH3:1][C:2]1([CH3:19])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[C:11]([CH2:15][C:16]([OH:18])=[O:17])[CH:12]=[CH:13][CH:14]=2)[O:3]1.C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:27][CH3:28]>CN(C=O)C.[Cl-].[Na+].O>[CH3:8][C:6]1([CH3:7])[C:2]([CH3:19])([CH3:1])[O:3][B:4]([C:9]2[CH:10]=[C:11]([CH2:15][C:16]([O:18][CH2:27][CH3:28])=[O:17])[CH:12]=[CH:13][CH:14]=2)[O:5]1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 35832052-(3-(Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetic acid

Product 1

HCID 53217140Ethyl 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetateYield 65%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetic acid (0.50 g, 1.91 mmol) in 20 mls of dry DMF was added cesium carbonate (1.24 g, 3.82 mmole) and iodoethane (0.20 mls, 2.48 mmol). This mixture was stirred at room temperature for 16 hours, then diluted with brine, extracted twice with EtOAc, extracts washed with brine (2×), dried over sodium sulfate and concentrated under reduced pressure to give 360 mgs (65%) of ethyl 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate as a clear oil.

Workup

  1. extractionextracted twice with EtOAc
  2. washextracts washed with brine (2×)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ba8dd237222a43058bdbe5112c7df798
Source dataset
uspto-grants-2014_04
Patent number
US08691809B2

Reaction notes

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