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

HRID 2275718Notes

Reaction equation

HRID 2275718 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-d8dc268ff5404ea196a37896c424046f
Source dataset
uspto-grants-2015_09
Patent number
US09126940B2

Reaction notes

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