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Dimethyl Ether → 3-Methoxy-4-(2-methoxyethoxy)phenylboronic acid

HRID 1175148
Notes
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Reaction equation

HRID 1175148 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([B:8]2[O:16]C(C)(C)C(C)(C)[O:9]2)=[CH:4][C:3]=1[O:17][CH3:18].[CH3:19][O:20][CH3:21].[C:22]([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CC(OC)(C)C.CCCCCCC>[CH3:18][O:17][C:3]1[CH:4]=[C:5]([B:8]([OH:9])[OH:16])[CH:6]=[CH:7][C:2]=1[O:1][CH2:22][CH2:19][O:20][CH3:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8254Dimethyl EtherHCID 10796Cesium carbonateHCID 27346502-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Product 1

HCID 666839933-Methoxy-4-(2-methoxyethoxy)phenylboronic acid

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent
HCID 22389680
MTBE heptane
Solvent

Procedure

4-Hydroxy-3-methoxyphenylboronic acid pinacol ester (Aldrich, 518786) (1 g; 4 mmol), 2-bromomethyl)-methylether (0.83 g; 6 mmol) and Cs2CO3 (2.6 g; 8 mmol) in DMF (10 ml) are heated to 130° C. for 45 minutes. The reaction mixture is diluted with TBME/heptane (5 ml/5 ml), filtered and evaporated to deliver the title compound as yellow oil used without further purification in Example 79.

Workup

  1. filtrationfiltered
  2. customevaporated
  3. customused without further purification in Example 79

Sources & evidence

ORD record
ord-2162e5bd9a1b4cfdad86ae80be1b76d2
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07838674B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes