تفاعل #425724

معادلة التفاعل

acetic acid

4-bromobenzaldehyde

3-buten-1-ol

hydrobromic acid

→

title compound

المردود 57.8%

4-bromo-2-(4-bromophenyl)tetrahydro-2H-pyran

المردود 57.8%

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   أخرىReaction
2. 2
   أخرىwas quenched by aqueous sodium bicarbonate
3. 3
   استخلاصextracted with ethyl acetate
4. 4
   غسيلwashed with brine
5. 5
   تجفيفdried over sodium sulfate
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated
8. 8
   أخرىThe residue was purified by silica gel chromatography

الإجراء التجريبي

To a solution of 4-bromobenzaldehyde (1.00 g, 5.41 mmol) and 3-buten-1-ol (800 mg, 10.8 mmol) in dichloromethane (20 mL) at room temperature was added zinc (II) bromide (25 mg, 0.11 mmol) followed by 33% hydrobromic acid (2.4 g) in acetic acid (4.9 g, 81 mmol) and stirred at room temperature for 5 hours. Reaction was quenched by aqueous sodium bicarbonate, then extracted with ethyl acetate, washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography to give the title compound (1.00 g) which contained some of 4-bromobenzaldehyde 1H NMR (400 MHz, CDCl3) δ ppm 7.49 (d, 2H) 7.24 (d, 2H) 5.19 (dd, 1H) 4.25 (m, 1H) 4.12 (m, 1H) 3.60 (m, 1H) 2.75 (m, 1H) 2.68 (m, 1H) 2.11 (m, 2H).

المصدر