Methyl morpholine oxide → Methyl 3,5-dibromo-4-formylbenzoate

HRID 394205

반응식

HRID 394205 반응식
Br[CH2:2][C:3]1[C:12]([Br:13])=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[Br:14].C[N+]1([O-])CC[O:19]CC1>C(#N)C.[Cl-].[Na+].O>[Br:14][C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([Br:13])[C:3]=1[CH:2]=[O:19])[C:7]([O:9][CH3:10])=[O:8]

참가 물질

5

반응물 2

HCID 82029Methyl morpholine oxideHCID 22647948444663-80-32회

생성물 1

HCID 22647908Methyl 3,5-dibromo-4-formylbenzoate

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 57417360Sodium chloride; water용매

반응 조건

온도
50 °C

실험 절차

Methyl 3,5-dibromo-4-(bromomethyl)benzoate (INTERMEDIATE 24) (3.9 g) was dissolved in acetonitrile (100 mL) and to this was added 4 Å molecular sieves and N-methylmorpholine N-oxide (1.18 g) and the reaction heated to 50° C. for 12 h. The reaction mixture was poured into brine and extracted into ethyl acetate, dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography eluting with 90% hexane:10% ethyl acetate to give the title compound. 1H NMR (500 MHz, CDCl3): δ 10.27 (s, 1H); 8.29 (s, 2H); 3.99 (s, 3H).

후처리

  1. extractionextracted into ethyl acetate
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with 90% hexane

출처 및 근거

ORD 기록
ord-552b45866d3a478b82a8275088fb5393
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06809199B2

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