Reaction #70276

Reaction equation

methyl 2-amino-5-bromobenzoate

cyclopropylboronic acid

K3PO4

P(Cy)3

→

expected product

Yield 88.3%

Methyl 2-amino-5-cyclopropylbenzoate

Yield 88.3%

Solvents

toluene

water

Conditions

Workup

1. 1
   FiltrationThe reaction mixture was filtered through celite
2. 2
   Otherthe organic phase was separated
3. 3
   Otherevaporated

Procedure

In a schlenck tube, a mixture of methyl 2-amino-5-bromobenzoate (43.47 mmol, 10 g), cyclopropylboronic acid (112.92 mmol, 9.700 g), K3PO4 (144.16 mmol, 30.6 g), Pd(AcO)2 (3.47 mmol, 0.780 g), P(Cy)3 (7.85 mmol, 2.2 g) in toluene (170 ml) and water (10 ml) was heated for 2 hours at 100° C., under nitrogen atmosphere. The reaction mixture was filtered through celite and the organic phase was separated and evaporated affording 7.34 g (yield 77%) of the expected product.

Source