Bromine → 2-Bromo-3,5-dimethoxybenzaldehyde

HRID 2061362ノート

反応式

HRID 2061362 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)[CH:6]=[O:7].[Br:13]Br>C(O)(=O)C>[Br:13][C:8]1[C:9]([O:11][CH3:12])=[CH:10][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[CH:6]=[O:7]

参加物

4

反応物 2

HCID 24408BromineHCID 817473,5-Dimethoxybenzaldehyde

生成物 1

HCID 114631512-Bromo-3,5-dimethoxybenzaldehyde収率 66%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒2 回

反応条件

温度
0 °C

実験手順

3,5-dimethoxybenzaldehyde (12.6 g, 76 mmol) was dissolved in acetic acid (350 mL). The resulting colourless solution was cooled to 0° C. A solution of bromine (3.9 mL) in acetic acid (50 mL) was added dropwise over 1 h. Once the addition was complete the ice bath was removed and the resulting pale green solution was stirred overnight at room temperature. Cold water was added to the solution. The resulting white solid was collected by vacuum filteration and rinsed with water. The solid was then redissolved in EtOAc and adsorbed on silica gel. The product was purified by flash chromatography, eluting with hexane/EtOAc (4:1) to give 37 (12.5 g, 66%) as a white solid. m/z=344.98 (M+H). 1H NMR (500 MHz, CDCl3): δ: 10.43 (1H, s, CHO), 7.06 (1H, s, ArH), 6.73 (1H, s, ArH), 3.93 (3H, s, CH3O), 3.86 (3H, s, CH3O). 13C NMR (500 MHz, CDCl3): δ: 192.09 (CHO), 159.92 (C-5), 157.02 (C-3), 134.67 (C-1), 109.12 (C-2), 105.83, 103.37 (C-4 & C-6), 56.60 (OMe), 55.82 (OMe).

後処理

  1. additionOnce the addition
  2. customwas removed
  3. additionCold water was added to the solution
  4. customThe resulting white solid was collected by vacuum filteration
  5. washrinsed with water
  6. dissolutionThe solid was then redissolved in EtOAc
  7. customThe product was purified by flash chromatography
  8. washeluting with hexane/EtOAc (4:1)

出典と根拠

ORDレコード
ord-7f7e0cd101dc47efb73fb6f9a2ba3a5c
出典データセット
uspto-grants-2012_10
特許番号
US08283340B2

反応ノート

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