Triethylamine → HCID 67024331, compound

HRID 1969209Notes

Reaction equation

HRID 1969209 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-c7f2d5cc76d44838aab06a8c4ef62bad
Source dataset
uspto-grants-2013_04
Patent number
US08426473B2

Reaction notes

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