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Water → Methyl 2-bromo-3,5-bis(methoxymethoxy)phenylacetate

HRID 495176
ノート
印刷プレビュー

反応式

HRID 495176 の反応式
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:8]=[C:9]([O:11][CH2:12][O:13][CH3:14])[CH:10]=1.[Br:20]N1C(=O)CCC1=O.O>CN(C)C=O>[CH3:14][O:13][CH2:12][O:11][C:9]1[C:8]([Br:20])=[C:7]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:6]=[C:5]([O:4][CH2:3][O:2][CH3:1])[CH:10]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 23116398Methyl 3,5-bis(methoxymethoxy)phenylacetate

生成物 1

HCID 68420121Methyl 2-bromo-3,5-bis(methoxymethoxy)phenylacetate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
4 °C

実験手順

Methyl 3,5-bis(methoxymethoxy)phenylacetate (43 g, 0.16 mol) obtained in Example 1, Step 1 was dissolved in N,N-dimethylformamide (0.68 L). After the solution was cooled to 4° C., N-bromosuccinimide (28 g, 0.16 mol) was added thereto, followed by stirring for 3 hours, while the temperature of the reaction mixture was raised to room temperature. To the reaction mixture was added water (0.50 L), and the mixture was extracted with a mixed solvent of hexane and ethyl acetate (hexane/ethyl acetate=1/2, 0.40 L×4). The organic layer was washed with a saturated aqueous solution of sodium chloride (50 mL) and dried over anhydrous sodium sulfate, followed by concentration under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/4-1/2) to obtain a quantitative yield of methyl 3,5-bis(methoxymethoxy)-2-bromophenyl-acetate.

後処理

  1. temperaturewas raised to room temperature
  2. extractionthe mixture was extracted with a mixed solvent of hexane and ethyl acetate (hexane/ethyl acetate=1/2, 0.40 L×4)
  3. washThe organic layer was washed with a saturated aqueous solution of sodium chloride (50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationfollowed by concentration under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/4-1/2)

出典と根拠

ORDレコード
ord-fd841cbea225467c8ba294a186da3e15
出典データセット
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07538224B2

反応ノート

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