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

HRID 394205ノート

反応式

HRID 394205 の反応式
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]

参加物

5

反応物 2

HCID 82029Methyl morpholine oxideHCID 22647948Methyl 3,5-dibromo-4-(bromomethyl)benzoate2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-552b45866d3a478b82a8275088fb5393
出典データセット
uspto-grants-2004_10
特許番号
US06809199B2

反応ノート

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