ChemicalBook CAS DataBase List 3-BROMOBENZOTHIOPHENE-2-CARBOXYLIC ACID&

3-BROMOBENZOTHIOPHENE-2-CARBOXYLIC ACID& synthesis

7synthesis methods

Product Name:3-BROMOBENZOTHIOPHENE-2-CARBOXYLIC ACID&
CAS Number:29174-66-1
Molecular formula:C9H5BrO2S
Molecular Weight:257.1

6314-28-9
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3-BROMOBENZOTHIOPHENE-2-CARBOXYLIC ACID&

29174-66-1
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$141.00/1g

Yield:29174-66-1 50%

Reaction Conditions:

with bromine;sodium acetate;acetic acid at 55 - 60; for 24 h;Inert atmosphere;

Steps:

(b) Preparation of 3-bromobenzo[b]thiophene-2-carboxylic acid (4):

To a solution of commercially available benzo[b]thiophene-2-carboxylic acid (1 g,5.61 mmol) and anhydrous NaOAc (1.0 g, 12.1 mmol) in glacial acetic acid(30 mL) was added bromine (2.48 g, 31.4 mmol) drop wise and slowly. The reaction mixture was stirred at 55-60 °C under nitrogen for 24 h. The mixture was poured into ice water (170 mL). The resulting precipitate was filtered, washed with cold water, (3 30 mL) and then EtOH (20 mL) and dried. The solid obtained was recrystallized from hot acetone to give the desired product as a colorless solid (yield 50%); mp 279-281 °C; 1H NMR (acetone-d6, 400 MHz)d 8.03-7.98 (m, 2H), 7.66-7.57 (m, 2H); 13C NMR (acetone-d6, 100 MHz) d161.8 (CO), 139.3, 138.6, 128.3, 125.7, 125.5, 122.7, 115.1; m/z (ES Mass) 257(M+1, 100%).

References:

Rao, Manam Sreenivasa;Haritha, Meda;Chandrasekhar;Basaveswara Rao, Mandava V.;Pal, Manojit [Tetrahedron Letters,2014,vol. 55,# 9,p. 1660 - 1663]

637-44-5 Synthesis