Sulfuric Acid → 7-Bromo-3-methylnaphthalen-1-ol

HRID 926202ノート

反応式

HRID 926202 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([CH3:16])=[CH:10][C:11]([O:13]CC)=O)=[CH:4][CH:3]=1.OS(O)(=O)=O>>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([CH:8]=[C:9]([CH3:16])[CH:10]=[C:11]2[OH:13])=[CH:6][CH:7]=1

参加物

3

反応物 2

HCID 1118Sulfuric AcidHCID 67126147Ethyl 4-(4-bromophenyl)-3-methylbut-2-enoate

生成物 1

HCID 671262827-Bromo-3-methylnaphthalen-1-ol

反応条件

温度
50 °C

実験手順

A flask containing the crude ethyl 4-(4-bromophenyl)-3-methylbut-2-enoate from above (˜30 grams) was treated with concentrated H2SO4 (120 mL) and warmed to 50° C. for 2.5 h. The reaction was poured onto ˜500 mL of crushed ice. Once the ice had thawed, the brown suspension was extracted with two portions of EtOAc (500 mL and 100 mL, respectively). The two extracts were combined, washed with saturated NaHCO3, dried (MgSO4), filtered, and concentrated to ˜55 mL. The residue was treated with DCM and loaded onto a silica gel column and purified by flash chromatography (ethyl acetate/hexanes) giving the desired product. 1H NMR (400 MHz, CDCl3) δ 8.29 (d, J=1.9 Hz, 1H), 7.57 (d, J=8.6 Hz, 1H), 7.50 (dd, J=8.6, 2.0 Hz, 1H), 7.17 (s, 1H), 6.67 (s, 1H), 2.42 (s, 3H).

後処理

  1. extractionthe brown suspension was extracted with two portions of EtOAc (500 mL and 100 mL
  2. washwashed with saturated NaHCO3
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated to ˜55 mL
  6. additionThe residue was treated with DCM
  7. custompurified by flash chromatography (ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-8fd3423e43d84f62a31b1cf6b85b3afa
出典データセット
uspto-grants-2016_03
特許番号
US09284323B2

反応ノート

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