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Sulfuric Acid → tert-Butyl 4-bromo-3-methoxybenzoate

HRID 1908102
ノート
印刷プレビュー

反応式

HRID 1908102 の反応式
[O-]S([O-])(=O)=O.[Mg+2].OS(O)(=O)=O.[Br:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][C:14]=1[O:22][CH3:23].[CH3:24][C:25](O)([CH3:27])[CH3:26]>C(Cl)Cl>[Br:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([O:19][C:25]([CH3:27])([CH3:26])[CH3:24])=[O:18])=[CH:15][C:14]=1[O:22][CH3:23]
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

6

反応物 4

HCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 24083Sulfuric acid magnesium salt (1:1)HCID 162158674-Bromo-3-methoxybenzoic acid

生成物 1

HCID 25307097tert-Butyl 4-bromo-3-methoxybenzoate収率 13.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane
溶媒

反応条件

温度
0 °C

実験手順

MgSO4 (4.82 g, 40.0 mmol), DCM (40 mL), and H2SO4 (533 μL, 10.0 mmol) were combined at 0° C. and the mixture was allowed to stir for 30 minutes at 0° C. 4-Bromo-3-methoxy-benzoic acid (2.31 g, 10.0 mmol) and 2-methylpropan-2-ol (4.78 mL, 50.0 mmol) were added and the mixture was allowed to stir at rt overnight. The mixture was filtered to remove the MgSO4 and the filtrate was washed with 1N NaOH. The layers were separated and the organic layer was dried over sodium sulfate and the solvent was removed to yield 400 mg of tert-butyl 4-bromo-3-methoxybenzoate. ESI-MS m/z calc. 286.0. found 287.0 (M+1)+; Retention time: 3.11 minutes (4 min run).

後処理

  1. customwere combined at 0° C.
  2. stirringto stir at rt overnight
  3. filtrationThe mixture was filtered
  4. customto remove the MgSO4
  5. washthe filtrate was washed with 1N NaOH
  6. customThe layers were separated
  7. dry with materialthe organic layer was dried over sodium sulfate
  8. customthe solvent was removed

出典と根拠

ORDレコード
ord-7259f1ec15464356898776b768ce5a04
出典データセット
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08598164B2

反応ノート

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