Ethyl Bromide → (5-Ethoxy-2-nitrophenyl)methanol

HRID 2375414

반응식

HRID 2375414 반응식
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([OH:12])[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].Br[CH2:14][CH3:15].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:14]([O:12][C:5]1[CH:6]=[CH:7][C:8]([N+:9]([O-:11])=[O:10])=[C:3]([CH2:2][OH:1])[CH:4]=1)[CH3:15]

참가 물질

5

반응물 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 1089463-(Hydroxymethyl)-4-nitrophenol

생성물 1

HCID 45091604(5-Ethoxy-2-nitrophenyl)methanol

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

To a solution of 3-hydroxymethyl-4-nitro-phenol (510 mg, 3.0 mmol) in 5 mL of dry DMF was added bromoethane (540 mg, 5.0 mmol) and K2CO3 powder (500 mg). The resulting reaction mixture was warmed to 50° C. and stirred for 1 h. It was quenched by addition of 20 mL of H2O, extracted with diethyl ether (2×20 mL). The combined organic extracts were washed with brine (50 mL), dried (MgSO4), filtered, and concentrated in vacuo to afford (5-ethoxy-2-nitro-phenyl)-methanol as a pale yellow oil: 1H NMR (CDCl3, 500 MHz) δ 8.20 (d, 1H), 7.36 (s, 1H), 6.89 (m, 1H), 5.00 (s, 2H), 4.16 (q, 2H), 2.57 (br t, 1H), 1.49 (t, 3H).

후처리

  1. customThe resulting reaction mixture
  2. customIt was quenched by addition of 20 mL of H2O
  3. extractionextracted with diethyl ether (2×20 mL)
  4. washThe combined organic extracts were washed with brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-4ab8845c5a1b403aada72f8e1412ef9b
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07465730B2

연결된 노트

불러오는 중…