تفاعل #531806

ord-dd77b5c646954f9197777bd4683773f4

معادلة التفاعل

BrCc1ccccc1
Benzyl bromide
COc1cc(Br)c(C=O)cc1O
2-Bromo-5-hydroxy-4-methoxybenzaldehyde
O=C([O-])[O-].[K+].[K+]
K2CO3
CC#N
acetonitrile
COc1cc(Br)c(C=O)cc1OCc1ccccc1
2
المردود 83.0%
COc1cc(Br)c(C=O)cc1OCc1ccccc1
5-Benzyloxy-2-bromo-4-methoxybenzaldehyde
المردود 83.0%

المذيبات

ظروف التفاعل

درجة الحرارة
50°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىflushed with Ar
  2. 2
    درجة الحرارةAfter cooling
  3. 3
    استخلاصextracted with CH2Cl2 (300 mL)
  4. 4
    غسيلThe CH2Cl2 was washed with water (3×100 mL)
  5. 5
    أخرىdried
  6. 6
    تركيزconcentrated
  7. 7
    أخرىRecrystallization with isopropanol: water (3:1)

الإجراء التجريبي

2-Bromo-5-hydroxy-4-methoxybenzaldehyde (25 g, 0.108 mol) and K2CO3 (30 g, 0.216 mol) were added to acetonitrile (250 mL) and flushed with Ar. Benzyl bromide (20 g, 0.12 mol) was added and the mixture was heated under Ar for 20 h at 50° C. After cooling, the mixture was poured into water (200 ml) and extracted with CH2Cl2 (300 mL). The CH2Cl2 was washed with water (3×100 mL), dried and concentrated. Recrystallization with isopropanol: water (3:1) gave 28.8 g (83%) of 2 as a light brown solid. 1H-NMR (400 MHz, CDCl3) dH 3.96 (3H, s, OCH3), 5.16 (2H, s, CH2Ph), 7.07-7.48 (7H, m, ArH+CH2Ph), 10.16 (1H, s, CHO).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08475776B2uspto-grants-2013_07