ChemicalBook CAS DataBase List Methyl 3-amino-5-bromobenzoate

Methyl 3-amino-5-bromobenzoate synthesis

5synthesis methods

Product Name:Methyl 3-amino-5-bromobenzoate
CAS Number:706791-83-5
Molecular formula:C8H8BrNO2
Molecular Weight:230.06

3-Bromo-5-aminobenzoic acid (1.0 g, 4.62 mmol) was stirred in methanol (15mL) with ice cooling, and the yellow solution was treated with thionyl chloride (4.00 mL, 55.0 mmol) dropwise over 20 mm. The resulting mixture was allowed to warm to room temperature and left stirring overnight. The reaction mixture was quenched with aqueous saturated NaHCO3 solution at 0 C. The solvent was then removed under vacuum, and the residue was suspended in ethyl acetate (200 mL). The organic phase was washed with brine (100 mL), dried (Na2504) and concentrated to afford Methyl 3-amino-5-bromobenzoate as a yellow solid (1.08 g, 98%). NMR (400 MHz, Methanol-d) oe 7.10 (t, J 1.6 Hz, 1H), 6.83 (t, J 1.6 Hz, 1H), 6.57 (t, J= 1.6 Hz, 1H), 3.46 (s, 3H). 13C NMR (100 MHz, CDC13) oe: 52.3, 114.6, 121.6, 122.3, 122.9, 132.6, 147.7, 166.0. m/z (ESI, MH) 231.

121-92-6
607 suppliers
$6.00/25g

706791-83-5
113 suppliers
$8.00/250mg

Yield:-

Steps:

Multi-step reaction with 3 steps
1: sulfuric acid; N-Bromosuccinimide / 2 h / 60 °C
2: sodium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C
3: ammonium chloride; iron / ethanol; water / 1 h / 80 °C

References:

Kuntz, Kevin W.;Campbell, John E.;Keilhack, Heike;Pollock, Roy M.;Knutson, Sarah K.;Porter-Scott, Margaret;Richon, Victoria M.;Sneeringer, Chris J.;Wigle, Tim J.;Allain, Christina J.;Majer, Christina R.;Moyer, Mikel P.;Copeland, Robert A.;Chesworth, Richard [Journal of Medicinal Chemistry,2016,vol. 59,# 4,p. 1556 - 1564]

6307-87-5 Synthesis

6307-87-5
122 suppliers
$9.00/1g

706791-83-5
113 suppliers
$8.00/250mg

References

67-56-1 Synthesis

67-56-1
803 suppliers
$7.29/5ml-f

42237-85-4 Synthesis

42237-85-4
146 suppliers
$8.00/1g

706791-83-5
113 suppliers
$8.00/250mg

References

618-95-1
219 suppliers
$14.00/5g

706791-83-5
113 suppliers
$8.00/250mg

References

6307-83-1 Synthesis

6307-83-1
222 suppliers
$5.00/250mg

706791-83-5
113 suppliers
$8.00/250mg

References

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Methyl 3-amino-5-bromobenzoate synthesis

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