Methylparaben → HCID 65018946, compound

HRID 1255169Notes

Reaction equation

HRID 1255169 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[F:12][C:13]([F:24])([F:23])[C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C(N(CC)CC)C>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.ClCCl>[F:12][C:13]([F:24])([F:23])[C:14]1[CH:19]=[CH:18][C:17]([O:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=2)=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 7456MethylparabenHCID 8471TriethylamineHCID 27343894-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 65018946HCID 65018946, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A flask was charged with methyl 4-hydroxybenzoate (500 mg, 3.29 mmol), copper (II) acetate (895 mg, 4.93 mmol), 4-trifluoromethylphenylboronic acid (2.50 g, 13.15 mmol), and 4 angstrom molecular sieves (500 mg). Dichloromethane (33 mL) and triethylamine (1.83 mL, 13.15 mmol) were added, and the reaction mixture was stirred rapidly, open to air. After 48 h, the reaction mixture was filtered and concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 10% EtOAc in hexanes, then 10 to 100% EtOAc in hexanes) provided the title compound: LCMS m/z 297.5 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.07-8.05 (m, 2H), 7.63 (d, J=8.5 Hz, 2H), 7.12 (d, J=8.5 Hz, 2H), 7.06-7.04 (m, 2H), 3.92 (s, 3H).

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customPurification by flash chromatography on silica gel (0 to 10% EtOAc in hexanes

Sources & evidence

ORD record
ord-19134196a7aa4ed9b7ed9bd816e6a223
Source dataset
uspto-grants-2013_06
Patent number
US08455638B2

Reaction notes

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