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Acetonitrile → 5-(Benzyloxy)-2-bromo-4-methoxybenzaldehyde

HRID 444624
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HRID 444624 반응식
[Br:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([OH:12])=[CH:6][C:3]=1[CH:4]=[O:5].C([O-])([O-])=O.[K+].[K+].C(#N)C.[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O>[CH2:22]([O:12][C:7]1[C:8]([O:10][CH3:11])=[CH:9][C:2]([Br:1])=[C:3]([CH:6]=1)[CH:4]=[O:5])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1
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참가 물질

6

반응물 4

HCID 6342AcetonitrileHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 6160682-Bromo-5-hydroxy-4-methoxybenzaldehyde

생성물 1

HCID 109033195-(Benzyloxy)-2-bromo-4-methoxybenzaldehyde수율 83%

시약·촉매·용매 1

HCID 962Water용매

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온도
50 °C

실험 절차

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).

후처리

  1. customflushed with Ar
  2. temperatureAfter cooling
  3. extractionextracted with CH2Cl2 (300 mL)
  4. washThe CH2Cl2 was washed with water (3×100 mL)
  5. customdried
  6. concentrationconcentrated
  7. customRecrystallization with isopropanol: water (3:1)

출처 및 근거

ORD 기록
ord-dd77b5c646954f9197777bd4683773f4
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08475776B2

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