ChemicalBook CAS DataBase List 3-AMINO-2-BROMO-BENZOIC ACID METHYL ESTER

3-AMINO-2-BROMO-BENZOIC ACID METHYL ESTER synthesis

6synthesis methods

Product Name:3-AMINO-2-BROMO-BENZOIC ACID METHYL ESTER
CAS Number:106896-48-4
Molecular formula:C8H8BrNO2
Molecular Weight:230.06

5337-09-7 Synthesis

5337-09-7
100 suppliers
$20.00/250mg

3-AMINO-2-BROMO-BENZOIC ACID METHYL ESTER

106896-48-4
86 suppliers
$20.00/100mg

Yield: 98%

Reaction Conditions:

with tin(ll) chloride in methanol;water for 2 h;Heating / reflux;

Steps:

5.1 Step 1. Preparation OF 3-AMINO-2-BROMO-BENZOIC acid methyl ester 5 (a)
2-Bromo-3-nitro-benzoic acid methyl ester (12.9 g, 49.5 MMOL) (prepared from 2-amino-3-nitro- benzoic acid as described by Webber E. S. et AL., see patent application number WO 01/16136 A2) and SNCI2 (42 g, 223 MMOL) were REFLUXED in methanol (225 mL, 0.2 M) and H20 (5.3 G, 243 MMOL) for 2 hours. After cooling at ambient temperature, diatomaceous earth (20 G) and DICHLOROMETHANE (1 L) were added followed with 3N aqueous sodium hydroxide (150 mL) with vigorous stirring. The mixture was filtered and the organic phase was washed with saturated aqueous sodium chloride. The organic solution was dried over sodium sulfate, filtered and all volatiles were removed under reduced pressure to afford Intermediate 5 (a) (11.4 G) in 98% yield. 1H-NMR (d6-DMSO) : ? 7. 12 (dd, 1H, J = 8. 1,7. 5 Hz), 6.93 (dd, 1H, J = 8. 1,1. 6 Hz), 6.80 (dd, 1H, J = 7.4, 1.6 Hz), 5.57 (s, 2H), 3.81 (s, 3H).

References:

PFIZER INC. WO2004/63198, 2004, A1 Location in patent:Page 77

570-24-1 Synthesis