Water → 4-(3-Benzyloxyphenylthio)-2-chlorobenzaldehyde

3-Benzyloxybenzenethiol (13) (75.0 g, 347 mmol) and 2-chloro-4-fluorobenzaldehyde (55.0 g, 347 mmol) were dissolved in dimethylformamide (DMF) (350 mL) while the solution was being stirred. The solution was then placed in a water bath at 30° C. and potassium carbonate (62.3 g, 451 mmol) and dimethylformamide (25 mL) were added. This mixture was stirred for 30 min at an internal temperature of 40 to 42° C. Tap water (125 mL) was then added and the mixture was cooled in ice water. To the cooled mixture, additional tap water (625 mL) was added dropwise for crystallization. The mixture was stirred for 30 min and the resulting crystals were collected by filtration and washed with 10% aqueous 2-propanol (188 mL). The moist crystals were dissolved in ethyl acetate (750 mL) and the solution was washed twice with tap water (375 mL×2). The organic layer was concentrated under reduced pressure and acetone (900 mL) was added to the resulting residue. Purified water (386 mL) was then added dropwise at an internal temperature of 23° C. The mixture was stirred for 30 min and the resulting crystals were collected by filtration and washed with 50% aqueous acetone (400 mL). The washed crystals were air-dried overnight. Subsequently, the product was dried by blowing an air stream at 45° C. for 1 hour. This gave 4-(3-benzyloxyphenylthio)-2-chlorobenzaldehyde (1) as a colorless prism crystals (115 g, 94%).

1. customThe solution was then placed in a water bath at 30° C.
2. stirringThis mixture was stirred for 30 min at an internal temperature of 40 to 42° C
3. additionwas then added
4. stirringThe mixture was stirred for 30 min
5. filtrationthe resulting crystals were collected by filtration
6. washwashed with 10% aqueous 2-propanol (188 mL)
7. dissolutionThe moist crystals were dissolved in ethyl acetate (750 mL)
8. washthe solution was washed twice with tap water (375 mL×2)
9. concentrationThe organic layer was concentrated under reduced pressure and acetone (900 mL)
10. additionwas added to the resulting residue
11. additionPurified water (386 mL) was then added dropwise at an internal temperature of 23° C
12. stirringThe mixture was stirred for 30 min
13. filtrationthe resulting crystals were collected by filtration
14. washwashed with 50% aqueous acetone (400 mL)
15. customThe washed crystals were air-dried overnight
16. customSubsequently, the product was dried
17. customat 45° C.
18. customfor 1 hour

ORDレコード

ord-3fbb0698e2ed4612868d175f61bf0fde

出典データセット

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07795472B2