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

HRID 409084Notes

Reaction equation

HRID 409084 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), 4A 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-a07ac5475a8141a98f9f6ff1d7a1daa6
Source dataset
uspto-grants-2014_06
Patent number
US08759358B1

Reaction notes

Loading…