2-Chloro-3-nitrobenzoic acid → (2-Chloro-3-nitrophenyl)methanol

A solution of 2-chloro-3-nitrobenzoic acid (1.0 g, 5.0 mmol) in tetrahydrofuran (10 mL) is cooled to 0° C. under an argon atmosphere. Boranetetrahydrofuran complex (6.4 mL of a 1.0 M solution) is added dropwise, maintaining a reaction temperature of less than 5° C. After the addition is complete, the reaction mixture is stirred for 6 hours at room temperature. It is then cooled in an ice bath and quenched by the addition of 10 mL of 1.0 N HCl. The reaction mixture is heated at reflux for 30 minutes and concentrated by distilling the THF. The remaining aqueous solution is extracted with methylene chloride, and the organic layer is washed with saturated aqueous bicarbonate and brine. Evaporation of the organic layer followed by recrystallization of the residue from hexane gives 2-chloro-3-nitrobenzenemethanol (0.4 g, 43%), mp=69-70° C.

1. temperaturemaintaining a reaction temperature of less than 5° C
2. additionAfter the addition
3. temperatureIt is then cooled in an ice bath
4. customquenched by the addition of 10 mL of 1.0 N HCl
5. temperatureThe reaction mixture is heated
6. temperatureat reflux for 30 minutes
7. concentrationconcentrated
8. distillationby distilling the THF
9. extractionThe remaining aqueous solution is extracted with methylene chloride
10. washthe organic layer is washed with saturated aqueous bicarbonate and brine
11. customEvaporation of the organic layer
12. customfollowed by recrystallization of the residue from hexane

ORD record

ord-5709c87cd8b54e8e87d47d9e2fd155f4

Source dataset

uspto-grants-1991_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05017604