Water → 4-Methoxybenzo[d][1,3]dioxole

HRID 601016

反応式

HRID 601016 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([OH:9])[C:4]=1[OH:10].Br[CH2:12]Cl.O>CN(C=O)C>[CH3:1][O:2][C:3]1[C:4]2[O:10][CH2:12][O:9][C:5]=2[CH:6]=[CH:7][CH:8]=1

参加物

5

反応物 3

HCID 962WaterHCID 6333BromochloromethaneHCID 136223-Methoxycatechol

生成物 1

HCID 5924784-Methoxybenzo[d][1,3]dioxole

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 3-methoxy-benzene-1,2-diol (1.161 g, 8.28 mmol) in DMF (10 mL) was added to bromo-chloro-methane (611 ul, 1.1 equivalents) and stirred at 90 degrees Celsius for 4 hours. The mixture was poured into water and extracted with dichloromethane. The organic layer was poured thru a phase separator cartridge and concentrated to dryness. The crude product is a yellow liquid. The liquid was purified by column chromatography yielding 1.21 g, (96%). 1H-NMR (DMSO, 500 MHz) 6.7 (t, 1H), 6.63 (d, 1H), 6.58 (d, 1H), 5.97 (s, 2H), 3.83 (s, 3H) HPLC (method A) 2.86 min.

後処理

  1. extractionextracted with dichloromethane
  2. additionThe organic layer was poured thru a phase separator cartridge
  3. concentrationconcentrated to dryness
  4. customThe liquid was purified by column chromatography
  5. customyielding 1.21 g, (96%)
  6. custom1H-NMR (DMSO, 500 MHz) 6.7 (t, 1H), 6.63 (d, 1H), 6.58 (d, 1H), 5.97 (s, 2H), 3.83 (s, 3H) HPLC (method A) 2.86 min.

出典と根拠

ORDレコード
ord-8b088c76980d4f5fa34226426361b0f4
出典データセット
uspto-grants-2011_03
特許番号
US07902239B2

関連ノート

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