Sodium Bicarbonate → 3-(3-Hydroxyphenyl)indoline

Participants

Reaction Steps

A 3.0 g portion of the (+)-3-(3-methoxyphenyl)indoline obtained in Reference Example 4 was dissolved in 30 ml of dichloromethane, and this solution was added dropwise to 40 ml of a boron tribromide dichloromethane solution (1 mole/liter) at -70° C. After stirring the solution at room temperature overnight, ice water was added, the pH was adjusted to 9 with sodium bicarbonate, and the mixture was extracted with a chloroform/ethanol mixed solvent. After drying and concentration, ether was added to the residue to precipitate crystals which were then collected by filtration to obtain 2.7 g of 3-(3-hydroxyphenyl)indoline.

Provenance & Evidence