3-Bromo-5-fluorophenylacetonitrile synthesis
- Product Name:3-Bromo-5-fluorophenylacetonitrile
- CAS Number:305800-58-2
- Molecular formula:C8H5BrFN
- Molecular Weight:214.03
773837-37-9
0 suppliers
inquiry
216755-57-6
114 suppliers
$11.00/250mg
305800-58-2
27 suppliers
$52.89/250mg
Yield: 58%
Reaction Conditions:
in water;N,N-dimethyl-formamide at 75; for 3 h;Sealed tube;
Steps:
1.3
[001291 A suspension of sodium cyanide (0.38 g, 7.73 mmol) in water (0.35 mL) was treated with a solution of 3-bromo-5-fluorobenzyl bromide (1.38 g, 5.15 mmol) in dimethylformamide (2.6 mL), and the reaction was heated at 75°C in a sealed tube for 3 h. The reaction was cooled to room temperature and was partitioned between ethyl acetate (50 mL) and 2.5% w/v aqueous sodium bicarbonate (100 mL). The aqueous phase was extracted with a further portion of ethyl acetate (50 mL); and the combined extracts were washed with water (2 x 50 mL) and with saturated aqueous sodium chloride (50 mL); dried over sodium sulfate; filtered, and evaporated in vacuo to give the crude product. Purification on a BiotageTM 4OiM column (silica), eluting with 10% ethyl acetate/hexane, gave 2-[3-bromo-5-fluorophenyl]acetonitrile (0.64 g, 58%). 1H NMR (400 MHz, CDCI3): 67.26-7.28 (m, 1H), 7.17-7.19 & 7.19-7.21 (dm, JHF = 8.0 Hz, JHH = unresolved, 1H), 6.98- 7.00 & 7.00-7.02 (dm, JHF = 8.8 Hz, JHH = unresolved, 1H), 3.73 (s, 2H); 19F NMR (377 MHz, CDCI3): 6-109.46 (dd, JHF = 8.0, 8.0 Hz, 1 F); 13C NMR (101 MHz, CDCI3): 6 162.90 (d, JCF = 252.1 Hz), 133.95 (d, JCF = 8.5 Hz), 127.24 (d, JCF = 3.8 Hz), 123.53 (d, JCF 10.0 Hz), 119.22 (d, JCF = 23.8 Hz), 117.00, 114.50(d, JcF23.1 Hz), 23.30 (d, JCF 1.5 Hz).
References:
PROMETIC BIOSCIENCES INC.;GAGNON, Lyne;GROUIX, Brigitte WO2016/54728, 2016, A1 Location in patent:Paragraph 00129
216755-57-6
114 suppliers
$11.00/250mg
305800-58-2
27 suppliers
$52.89/250mg
176548-70-2
244 suppliers
$7.00/5g
305800-58-2
27 suppliers
$52.89/250mg
216755-56-5
105 suppliers
$10.00/1g
305800-58-2
27 suppliers
$52.89/250mg