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

HRID 926202노트

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HRID 926202 반응식
[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

참가 물질

3

반응물 2

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

생성물 1

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

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온도
50 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-8fd3423e43d84f62a31b1cf6b85b3afa
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09284323B2

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