Potassium Carbonate → 2-(2-Chloro-5-(2-methoxyethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 1094816

Reaction equation

HRID 1094816 reaction equation
[CH3:1][O:2][CH2:3][CH2:4]OS(C)(=O)=O.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:12]=1[B:18]1[O:22][C:21]([CH3:24])([CH3:23])[C:20]([CH3:26])([CH3:25])[O:19]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:4][CH2:3][O:2][CH3:1])=[CH:13][C:12]=1[B:18]1[O:22][C:21]([CH3:24])([CH3:23])[C:20]([CH3:26])([CH3:25])[O:19]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1462932-Methoxyethyl methanesulfonateHCID 534868364-Chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Product 1

HCID 575823372-(2-Chloro-5-(2-methoxyethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Methanesulfonic acid 2-methoxyethyl ester (70.5 mg, 0.50 mmol) and 2-[2-chloro-5-hydroxyphenyl]-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane (Preparation 66,100 mg, 0.42 mmol) were stirred together in N,N-dimethylacetamide (4 ml). Potassium carbonate (58 mg, 0.42 mmol) was added and the resultant solution was heated to 100° C. for 10 hours. The reaction mixture was cooled then quenched with water (10 ml) and extracted with ethylacetate (10 ml). The organic layer was dried over anhydrous MgSO4 (s), filtered and evaporated in vacuo to give crude title compound. Material taken on without further purification.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthen quenched with water (10 ml)
  3. extractionextracted with ethylacetate (10 ml)
  4. dry with materialThe organic layer was dried over anhydrous MgSO4 (s)
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-23207f8d35724c8bb5b85572a84a2b42
Source dataset
uspto-grants-2012_03
Patent number
US08134007B2

Linked notes

Loading…