Triethylamine → HCID 67024331, compound

HRID 1513122Notes

Reaction equation

HRID 1513122 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]=1[CH3:13].[Br:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[C:20]([O:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH:21]=1.C(N(CC)CC)C>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:18]2[CH:19]=[C:20]([O:22][CH2:23][CH:24]([CH3:25])[CH3:26])[CH:21]=[C:16]([Br:15])[CH:17]=2)=[CH:8][C:7]=1[CH3:13]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 23549552Methyl 2-(4-hydroxy-2-methylphenoxy)acetateHCID 53216316[3-Bromo-5-(2-methylpropoxy)phenyl]boronic acid

Product 1

HCID 67024331HCID 67024331, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

(4-Hydroxy-2-methyl-phenoxy)-acetic acid methyl ester (215 mg; 1.1 mmol), 3-Bromo-5-isobutoxy-phenylboronic acid (523.4; 1.9 mmol), copper(II) acetate (199 mg; 1.1 mmol), crushed molsieves (about 1 g) and triethylamine (0.46 ml; 3.3 mmol) was dissolved in dichloromethane (40 ml) and stirred over night. The reaction mixture was filtered through celite and evaporated to dryness. The crude product was purified by preparative HPLC (method B). Yield: 300 mg; 65%. HPLC-MS: m/z: 423.5 (M+); Rt: 2.71 min

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customevaporated to dryness
  3. customThe crude product was purified by preparative HPLC (method B)

Sources & evidence

ORD record
ord-a54ac932a088490f851428c7e9ba44b8
Source dataset
uspto-grants-2012_07
Patent number
US08217086B2

Reaction notes

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