ChemicalBook CAS DataBase List tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylate

tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylate synthesis

13synthesis methods

Product Name:tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylate
CAS Number:114772-40-6
Molecular formula:C18H19BrO2
Molecular Weight:347.25

TERT-BUTYL 4'-METHYLBIPHENYL-2-CARBOXYLATE

114772-36-0

114772-40-6

The general procedure for the synthesis of tert-butyl 4'-bromomethylbiphenyl-2-carboxylate from tert-butyl 4'-methyl-[1,1'-biphenyl]-2-carboxylate was as follows: in a 1200-liter enameled stirring apparatus, 268.0 kg of tert-butyl 4'-methyl-[1,1'-biphenyl]-2-carboxylate, 157.3 kg of N-bromosuccinimide (DDH), 1.6 kg of azo diisobutyronitrile (AIBN), and 572 liters of methyl acetate. The mixture was heated to 60 °C until the solution became almost colorless. Subsequently, 458 liters of solvent were distilled at atmospheric pressure, followed by the addition of 530 liters of isopropanol, 148 liters of water and 16.4 kg of anhydrous sodium acetate. The resulting mixture was cooled to 15 °C to 25 °C and stirring was continued for 1 hour. The precipitated product was separated by centrifugation, washed with a mixture of 530 liters of acetone and 148 liters of water and finally dried. 295 kg of tert-butyl 4'-bromomethylbiphenyl-2-carboxylate was obtained in a yield of 85% of the theoretical value.

114772-36-0
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$90.00/10mg

114772-40-6
202 suppliers
$7.00/1g

Yield:114772-40-6 85%

Reaction Conditions:

with azobisisobutyronitrile;sodium acetate in acetic acid methyl ester;water;isopropyl alcohol;acetone

Steps:

4 EXAMPLE 4
EXAMPLE 4 268.0 kg of tert-butyl 4-methylbiphenyl-2'-carboxylate, 157.3 kg of DDH, 1.6 kg of AIBN, and 572 liters of methyl acetate are placed in a 1200-liter enamel stirring apparatus and the mixture is heated to 60° C. to 65° C. As soon as the solution has become practically colorless, 458 liters of solvent are distilled off under normal pressure and then 530 liters of isopropanol, 148 liters of water, and 16.4 kg of sodium acetate (anhydrous) are added. The resulting mixture is cooled to 15° C. to 25° C. and stirred for a further 1 hour. The product precipitated is separated by centrifugation, washed with a mixture of 530 liters of acetone and 148 liters of water, and dried. Yield: 295 kg of tert-butyl 4-bromomethylbiphenyl-2'-carboxylate (85% of theory).

References:

Schneider, Heinrich;Schneider, Margarete US2002/95042, 2002, A1

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55666-42-7 Synthesis