تفاعل #7005

معادلة التفاعل

3′-fluoro-4′-methoxyacetophenone

m-chloroperbenzoic acid

LiOH.H2O

H2O

→

3-fluoro-4-methoxy phenol

المردود 72.7%

المذيبات

CH2Cl2

MeOH

ظروف التفاعل

المعالجة

1. 1
   غسيلThe solution was washed with saturated aqueous Na2CO3
2. 2
   ترشيحfiltered through a pad of SiO2 (CH2Cl2 as eluent)
3. 3
   أخرىfinally chromatographed (SiO2; hex:EtOAc 4:1)
4. 4
   أخرىto give the crude product (3′-fluoro-4′-methoxy phenyl acetate; 63 g)
5. 5
   أخرىVolatiles were removed in vacuo
6. 6
   أخرىthe residue was partitioned between excess aqueous 1 M HCl and EtOAc (aqueous layer pH˜3)
7. 7
   استخلاصThe aqueous phase was extracted with EtOAc (2×)
8. 8
   تجفيفThe combined organic extracts were dried (Na2SO4)
9. 9
   تركيزconcentrated in vacuo

الإجراء التجريبي

A solution of 3′-fluoro-4′-methoxyacetophenone (10 g; 59 mmol) and m-chloroperbenzoic acid (50% purity; 30 g; 89 mmol) in CH2Cl2 (300 mL) was stirred at RT overnight. The solution was washed with saturated aqueous Na2CO3, then filtered through a pad of SiO2 (CH2Cl2 as eluent) and finally chromatographed (SiO2; hex:EtOAc 4:1) to give the crude product (3′-fluoro-4′-methoxy phenyl acetate; 63 g). A solution of this crude material and LiOH.H2O (5 g; 120 mmol) in MeOH:H2O (100 mL of a 9:1 mixture) was stirred at RT overnight. Volatiles were removed in vacuo, and the residue was partitioned between excess aqueous 1 M HCl and EtOAc (aqueous layer pH˜3). The aqueous phase was extracted with EtOAc (2×). The combined organic extracts were dried (Na2SO4) and concentrated in vacuo to give 3-fluoro-4-methoxy phenol (6.1 g; 72%) as an oil.

المصدر