(4-Methoxyphenyl)boronic acid → Ethyl 4-methoxyphenylacetate

HRID 1892467Notes

Reaction equation

HRID 1892467 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.CCCCCC.[C:18]([O:21][CH2:22][CH3:23])(=[O:20])[CH3:19]>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:19][C:18]([O:21][CH2:22][CH3:23])=[O:20])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 201262(4-Methoxyphenyl)boronic acidHCID 21226206Ethyl acetate hexane

Product 1

HCID 84174Ethyl 4-methoxyphenylacetate

Procedure

Ethyl 4-methoxyphenylacetate was prepared by the general experimental method from 4-methoxyphenylboronic acid (152 mg, 1.00 mmol). After workup by column chromatography (hexane/ethyl acetate, 5:1), ethyl 4-methoxyphenylacetate is obtained as a colourless liquid in a yield of 77% of theory. 1H NMR (200 MHz, CDCl3): δ=7.25 (d, J=8.5 Hz, 2H), 6.91 (d, J=8.7 Hz, 2H), 4.13-4.26 (m, 2H), 3.82 (s, 3H), 3.59 (s, 2H), 1.24-1.26 (m, 3H) ppm; 13C NMR (50 MHz, CDCl3): δ=172.3, 159.1, 130.7, 126.7, 114.4, 61.1, 55.6, 40.9, 14.6 ppm; MS (70 eV), m/z (%): 194 (24) [M+], 121 (100), 91 (8), 77 (10), 51 (4); IR (NaCl): ν=2981 (m), 2836 (w), 1732 (s), 1513 (s), 1247 (m), 1032 (m) cm−1; elemental analysis: (theor): C=68.02, H=7.27, (exp): C=67.91, H=7.18.

Sources & evidence

ORD record
ord-a4d8ade6e273457482f72be4e4768b69
Source dataset
uspto-grants-2013_08
Patent number
US08507688B2

Reaction notes

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