Bromoacetic Acid → HCID 21252463, compound

Sodium (23 g, 1.0 mole) in form of chips was added in portions to diethylene glycol (500 ml) under nitrogen atmosphere. When the sodium had reacted completely, the mixture was cooled to room temperature and bromoacetic acid was added (76 g, 0.5 mole) under stirring. After 18 hours at 100° C. the excess of diethylene glycol was distilled off at about 4 mm Hg. Thereafter isopropyl alcohol (400 ml) and in portions acetyl chloride (51 g, 0.65 mole) were added. After stirring for 18 hours at 65° C. the mixture was cooled to room temperature and neutralized with sodium acetate (3.5 g, 0.15 mole). The mixture was filtered and the filtrate evaporated nearly to dryness, whereupon it was dissolved in water (200 ml). The water phase was extracted with 1,1,1-trichloroethane (3×50 ml). The pooled organic phases were washed with water (20 ml). The product was extracted from the pooled water phases with dichloromethane (50 ml) that after evaporation gave an oil (55 g).

1. distillationAfter 18 hours at 100° C. the excess of diethylene glycol was distilled off at about 4 mm Hg
2. stirringAfter stirring for 18 hours at 65° C. the mixture
3. filtrationThe mixture was filtered
4. customthe filtrate evaporated nearly to dryness, whereupon it
5. dissolutionwas dissolved in water (200 ml)
6. extractionThe water phase was extracted with 1,1,1-trichloroethane (3×50 ml)
7. washThe pooled organic phases were washed with water (20 ml)
8. extractionThe product was extracted from the pooled water phases with dichloromethane (50 ml) that
9. customafter evaporation

ORD record

ord-2a3401c745304d03995f6aac0800be29

Source dataset

uspto-grants-1999_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05858363