تفاعل #159784

معادلة التفاعل

aluminum chloride

chroman

2-bromo-5-iodobenzoic acid

oxalyl chloride

→

(2-bromo-5-iodo-phenyl)-chroman-6-yl-methanone

المردود 88.5%

المذيبات

DCM

DMF

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONAfter complete addition
2. 2
   أخرىThe volatiles were evaporated under reduced pressure
3. 3
   workup.DISSOLUTIONthe crude product was dissolved in DCM (4 mL)
4. 4
   درجة الحرارةhad been cooled to 0° C
5. 5
   workup.STIRRINGAfter stirring for 4 h
6. 6
   أخرىthe reaction was quenched
7. 7
   workup.ADDITIONby pouring it
8. 8
   أخرىinto crushed ice
9. 9
   استخلاصThis was extracted with dichloromethane (50 mL×2)
10. 10
    غسيلwashed with water (20 mL), saturated aqueous sodium bicarbonate solution (20 mL×2), and brine (20 mL)
11. 11
    تجفيفdried over sodium sulfate
12. 12
    تركيزconcentrated
13. 13
    أخرىThe crude product was purified by column chromatography

الإجراء التجريبي

To a stirred solution of 2-bromo-5-iodobenzoic acid (1.0 g, 3.06 mmol) in DCM (5 mL) was added DMF (0.2 mL) and oxalyl chloride (0.44 mL, 4.59 mmol) at 0° C. After complete addition, the reaction mixture was stirred at room temperature for 3 h. The volatiles were evaporated under reduced pressure, and the crude product was dissolved in DCM (4 mL) and added to chroman (488 mg, 3.67 mmol) which had been cooled to 0° C. To this mixture was added aluminum chloride (488 mg, 3.67 mmol) in portions. After stirring for 4 h, the reaction was quenched by pouring it into crushed ice. This was extracted with dichloromethane (50 mL×2). The dichloromethane layers were combined and washed with water (20 mL), saturated aqueous sodium bicarbonate solution (20 mL×2), and brine (20 mL), then dried over sodium sulfate, and concentrated. The crude product was purified by column chromatography to furnish (2-bromo-5-iodo-phenyl)-chroman-6-yl-methanone (1.2 g).

المصدر