تفاعل #48718

معادلة التفاعل

n-butyl lithium

1-bromo-3-fluoro-5-benzyloxy-benzene

N,N-dimethylformamide

→

desired compound

المردود 32.0%

3-benzyloxy-5-fluoro-benzaldehyde

المردود 32.0%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooled in a dry ice/acetone bath
2. 2
   درجة الحرارةmaintaining the internal temperature <−70°
3. 3
   workup.STIRRINGStir 30 minutes
4. 4
   أخرىremove cold bath
5. 5
   workup.WAITAfter 1 hour
6. 6
   أخرىquench with saturated aqueous ammonium chloride
7. 7
   تجفيفDry (sodium sulfate)
8. 8
   ترشيحfilter
9. 9
   تركيزconcentrate to an oil
10. 10
    أخرىPurify on 120 g silica gel eluting with 100:0 to 90:10 hexanes

الإجراء التجريبي

Add n-butyl lithium (35 mL, 1.6M, 55.96 mmol) over 15 minutes to 1-bromo-3-fluoro-5-benzyloxy-benzene (14.30 g, 50.87 mmol) in tetrahydrofuran (300 mL) cooled in a dry ice/acetone bath, maintaining the internal temperature <−70°. Stir 30 minutes and add N,N-dimethylformamide (7.44 g, 101.74 mmol). Stir 30 minutes and remove cold bath. After 1 hour, quench with saturated aqueous ammonium chloride. Wash organic layer with water and saturated aqueous sodium chloride. Dry (sodium sulfate), filter and concentrate to an oil. Purify on 120 g silica gel eluting with 100:0 to 90:10 hexanes:ethyl acetate to give 3.75 g (32%) of the desired compound as an oil.

المصدر