ChemicalBook CAS DataBase List Methyl 2,6-Difluoro-3-iodobenzoate

Methyl 2,6-Difluoro-3-iodobenzoate synthesis

5synthesis methods

Product Name:Methyl 2,6-Difluoro-3-iodobenzoate
CAS Number:501433-14-3
Molecular formula:C8H5F2IO2
Molecular Weight:298.03

67-56-1 Synthesis

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229178-74-9 Synthesis

229178-74-9
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501433-14-3
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$132.00/500mg

Yield:501433-14-3 92%

Reaction Conditions:

with thionyl chloride at 0; for 3 h;Reflux;

Steps:

5.3. Methyl 2,6-difluoro-3-iodobenzoate (4)

To a mixture of 2,6-difluoro-3-iodobenzoic acid 3 (2.84 g, 10.0 mmol) in methanol (30 mL) was added SOCl₂ (0.1 mL) dropwise at 0 °C. After being stirred at reflux for 3 h, the mixture was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate 15:1 to 10:1, v/v) to give the desired compound 4 as a white solid (2.75 g, 92%): mp 54-55 °C (lit.⁶ mp 53-55 °C); ¹H NMR (CDCl₃) δ 3.95 (s, 3H, CH₃), 6.78-6.82 (t, 1H, J = 8.4 Hz, ArH), 7.78-7.83 (m, 1H, ArH); ¹³C NMR (CDCl₃) δ 53.10, 75.42, 75.46, 75.69, 75.73 (dd, J_C_-_F = 4.2, inlMMLBox = 26.8 Hz), 111.49, 111.69, 111.89 (t, J_C_-_F = 19.8 Hz), 113.81, 113.84, 114.03, 114.07 (dd, J_C_-_F = 3.9, inlMMLBox = 22.4 Hz), 141.42, 141.45, 141.51, 141.54 (dd, J_C_-_F = 3.1, inlMMLBox = 9.4 Hz), 157.99, 158.05, 160.52, 160.58 (dd, J_C_-_F = 6.2, inlMMLBox = 252.6 Hz), 159.48, 159.53, 162.04, 162.09 (dd, J_C_-_F = 5.1, inlMMLBox = 256.2 Hz), 161.16; GC-MS: 298 M⁺.

References:

He, Qiu-Qin;Gu, Shuang-Xi;Liu, Jia;Wu, Hai-Qiu;Zhang, Xuan;Yang, Liu-Meng;Zheng, Yong-Tang;Chen, Fen-Er [Bioorganic and Medicinal Chemistry,2011,vol. 19,# 16,p. 5039 - 5045] Location in patent:experimental part

67-56-1 Synthesis

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