Triethylamine → 2-(4-(3-Fluorophenoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 1187571Notes

Reaction equation

HRID 1187571 reaction equation
[CH3:1][C:2]1([CH3:16])[O:6][B:5]([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[O:4][C:3]1([CH3:15])[CH3:14].[F:17][C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=1.C(N(CC)CC)C>ClCCl>[F:17][C:18]1[CH:23]=[C:22]([CH:21]=[CH:20][CH:19]=1)[O:13][C:10]1[CH:11]=[CH:12][C:7]([B:5]2[O:4][C:3]([CH3:15])([CH3:14])[C:2]([CH3:16])([CH3:1])[O:6]2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27339863-Fluorophenylboronic acidHCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Product 1

HCID 710152102-(4-(3-Fluorophenoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneYield 25.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 250 mL round-bottom flask, was placed a solution of 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (5 g, 22.72 mmol, 1.00 equiv) in dichloromethane (100 mL), (3-fluorophenyl)boronic acid (3.5 g, 25.01 mmol, 1.10 equiv), Cu(AcO)2 (5 g), 4 A molecular sieves (15 g), and triethylamine (4.6 g). The resulting solution was stirred overnight at room temperature. The solids were filtered out and the filtrate was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was loaded onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:100-1:50) to give 1.8 g (25%) of 2-[4-(3-fluorophenoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane as a colorless oil.

Workup

  1. customInto a 250 mL round-bottom flask, was placed
  2. filtrationThe solids were filtered out
  3. dry with materialthe filtrate was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum
  5. washeluted with ethyl acetate/petroleum ether (1:100-1:50)

Sources & evidence

ORD record
ord-08fbc207df894d12a2676604ac309025
Source dataset
uspto-grants-2014_03
Patent number
US08673925B1

Reaction notes

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