반응 #69454

반응 방정식

HCl

methyl 3-bromo-4-hydroxybenzoate

triethylamine

1-(vinyloxy)butane

→

methyl 3-acetyl-4-hydroxybenzoate

수율 82.0%

용매

ether

DCM

ethanol

반응 조건

후처리

1. 1
   온도The reaction was cooled down
2. 2
   여과filtered
3. 3
   농축the filtrate concentrated
4. 4
   workup.ADDITIONwas added
5. 5
   workup.STIRRINGStirring
6. 6
   온도was maintained for 2 h
7. 7
   기타the organic phase was separated
8. 8
   건조dried over MgSO4
9. 9
   여과filtered
10. 10
    농축concentrated
11. 11
    기타to afford a solid which
12. 12
    여과The solid was filtered off
13. 13
    농축the filtrate concentrated to dryness

실험 절차

To a degassed solution of methyl 3-bromo-4-hydroxybenzoate (350 g, 1514.87 mmol) in ethanol (3 L) were added triethylamine (0.528 L, 3787.17 mmol), 1-(vinyloxy)butane (0.588 L, 4544.60 mmol), 1,1′-bis(diphenylphosphino)ferrocene (33.1 g, 60.6 mmol) and diacetoxypalladium (8.50 g, 37.9 mmol) under nitrogen. The mixture was heated at 70° C. overnight. The reaction was cooled down, filtered and the filtrate concentrated. The resulting solid was solubilized with DCM (2 L) and HCl 4N (1.14 L, 4544 mmol) was added under stirring. Stirring was maintained for 2 h, the organic phase was separated, dried over MgSO4, filtered and concentrated to afford a solid which was stirred in ether (5 L) for 2 h. The solid was filtered off and the filtrate concentrated to dryness to afford methyl 3-acetyl-4-hydroxybenzoate (240 g, 82%) as a beige powder. Mass spectrum: m/z [M−H]−=193.

출처