Water → HCID 22999277, compound

Temperature

70 °C

1,2-Dibromoethane (62 mL, 0.72 moles) was added to a mixture of 3,5-dibromo-4-hydroxybenzaldehyde (10 g, 36 mmoles) and potassium carbonate (25 g, 180 mmoles) in DMF (100 ml) and the resulting mixture was stirred vigorously at 70° C. for 16 hours. After cooling, the mixture was poured into water (300 mL) and extracted with ethyl acetate (400 mL). Water (200 mL) was added to the aqueous phase and this was extracted with ethyl acetate (150 mL). The combined organic phases were washed with saturated sodium chloride (3×150 mL), dried over MgSO4 and evaporated in vacuo. The residue was dissolved in refluxing 96% ethanol (60 mL). Water (15 mL) was added and after cooling, filtration, washing with 60% ethanol and drying 10.7 g (77%) of 4-(2-bromoethoxy)-3,5-dibromobenzaldehyde was isolated in two crops. M.p. 84-85° C.

1. temperatureAfter cooling
2. extractionextracted with ethyl acetate (400 mL)
3. additionWater (200 mL) was added to the aqueous phase
4. extractionthis was extracted with ethyl acetate (150 mL)
5. washThe combined organic phases were washed with saturated sodium chloride (3×150 mL)
6. dry with materialdried over MgSO4
7. customevaporated in vacuo
8. dissolutionThe residue was dissolved
9. temperaturein refluxing 96% ethanol (60 mL)
10. additionWater (15 mL) was added
11. temperatureafter cooling
12. filtrationfiltration
13. washwashing with 60% ethanol
14. dry with materialdrying 10.7 g (77%) of 4-(2-bromoethoxy)-3,5-dibromobenzaldehyde
15. customwas isolated in two crops

ORD record

ord-7a2ab46ae2bc41408376b7611210e4dc

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06613942B1