1-Бром-2 ,3-дифторбензол

Химические свойства

Clear colorless to peach liquid

Использование

1-Bromo-2,3-difluorobenzene may be used in the synthesis of potent, orally active Calcitonin gene-related peptide (CGRP) receptor antagonist (BMS-846372). It may be used in the preparation of 2,3-difluorophenyl(dimethyl)phosphane.

Общее описание

Microbial oxidation of 1-bromo-2,3-difluorobenzene by Pseudomonas putida strain 39/D and Escherichia coli recombinant microorganism (strain JM 109(pDTG601)) has been reported.

Синтез

Add 50% aqueous solution of KOH (18.0 g, 160 mmol) to a mixture of 1-bromo-5,5,6,6-tetrafluorocyclohex-1-ene (11.65 g) and triethylbenzylammonium chloride (0.15 g, 0.7 mmol) at 30-35°C for 30 minutes. Keep the reaction mixture at 75-85°C for 2 hours. Cool the reaction mixture. Dilute the reaction mixture with water. Extract the organic product with CH2Cl2. Dry the organic product over CaCl2. Distill the organic product. 1H NMR (CDCl3, 300.1 MHz), δ: 7.00-7.16 (m, 1H, Ar); 7.17-7.29 (m, 1H, Ar); 7.34-7.47 (m, 1H, Ar). 13C NMR (CDCl3, 75.5 MHz), δ: 110.40 (d, C(1), J = 17.5 Hz); 116.40 (d, C(4), J = 17.7 Hz); 124.70 (dd, C(5), J = 7.1 Hz, J = 5.0 Hz); 128.23 (d, C(6), J = 3.6 Hz); 148.10 (dd, C(2), J = 248.8 Hz, J = 14.3 Hz); 150.92 (dd, C(3), J = 251.9 Hz, J = 13.3 Hz). 19F NMR (CDCl3, 282.4 MHz), δ: -130.9 (m, 1 F, Ar), -134.8 (m, 1 F, Ar). BP 157-158°C. Elemental Analysis Found (%): C, 37.54; H, 1.50. C6H3BrF2. Calculated (%): C, 37.34; H, 1.52. Mass Spec MS, m/z (Irel (%)): 194, 192 [M]+ (100, 99), 113 [M-Br]+ (88), 63 (60).
Fig The synthetic method of 1-Bromo-2,3-difluorobenzene

хранилище

Keep container sealed and store in an ventilated, low temperature, dry warehouse, separate from foods and oxidizing agents.