Ethyl bromoacetate → HCID 54754374, compound

HRID 1892464Notes

Reaction equation

HRID 1892464 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5](B(O)O)=[C:4]([CH3:12])[CH:3]=1.[F-].[K+].Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]>CCCCCC.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:4]([CH3:12])[CH:3]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 522689Potassium FluorideHCID 53216717(4-Chloro-2,6-dimethylphenyl)boronic acid

Product 1

HCID 54754374HCID 54754374, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Ethyl 4-chloro-2,6-dimethylphenylacetate was prepared by the general experimental method from 4-chloro-2,6-dimethylphenylboronic acid (186 mg, 1.00 mmol). This involved using 290 mg [5 mmol] of KF and 418 mg [2.5 mmol] of ethyl bromoacetate. After workup by column chromatography (hexane/ethyl acetate, 5:1), ethyl 4-chloro-2,6-dimethylphenylacetate is obtained as a colourless liquid in a yield of 68% of theory. 1H NMR (400 MHz, CDCl3): δ=7.02 (s, 2H), 4.13 (q, J=0.7 Hz, 2H), 3.62 (s, 2H), 2.29 (s, 6H), 1.23 (t, J=7.2 HZ, 3H) ppm; 13C NMR (101 MHz, CDCl3): δ=170.8, 139.0, 132.2, 131.6, 130.3, 127.9, 113.6, 60.8, 35.0, 20.1, 14.2 ppm; MS (70 eV), m/z (%): 226 (22) [M+], 180 (9), 153 (100), 115 (17), 91 (11); IR (NaCl): ν=2980 (m), 1733 (s), 1328 (w), 1155 (m), 1030 (m) cm−1; elemental analysis: (theor): C=63.58, H=6.67, (exp): C=63.30, H=6.78.

Sources & evidence

ORD record
ord-36d8f645eed947abbb9b26dc0f8e2843
Source dataset
uspto-grants-2013_08
Patent number
US08507688B2

Reaction notes

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