2-Bromoethanol → 4-((2-Hydroxyethyl)thio)phenol

HRID 330712노트

반응식

HRID 330712 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.Br[CH2:10][CH2:11][OH:12].C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[OH:12][CH2:11][CH2:10][S:8][C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=1

참가 물질

5

반응물 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 2401474-Mercaptophenol

생성물 1

HCID 130526324-((2-Hydroxyethyl)thio)phenol수율 72%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

(FIG. 2) (a) (4-(2-hydroxyethylsulfanyl) phenol) was synthesized by a modified literature procedure (pl add ref). 4-hydroxythiophenol (mercaptophenol) (6.00 g, 47.61 mmole), 2-bromoethanol (5.90 g, 47.6 mmol) and K2CO3 (6.6 g, 47.48 mmol) was stirred in dimethylformamide (DMF, 50 ml) at −5° C. for 30 minutes. The reaction mixture was then stirred for 12 hours at room temperature. The reaction mixture was poured in ice water (300 ml) and extracted with dichloromethane (DCM) (3×50 ml). The organic part was dried by MgSO4 and then solvent was removed under a rotary evaporator. The crude product was purified on silica gel column by using a chloroform/methanol (94:6) solvent mixture. Yield: 72%. 1H NMR (CDCl3): δ, 8.01 (s, OH, 1H), 7.33 (d, 2H, J=8.7 Hz), 6.78 (d, 2H, J=8.7 Hz), 4.52 (s, OH, 1H), 3.67 (t, 2H, J=6 Hz), 2.99 (t, 2H, J=5.7).

후처리

  1. extractionextracted with dichloromethane (DCM) (3×50 ml)
  2. dry with materialThe organic part was dried by MgSO4
  3. customsolvent was removed under a rotary evaporator
  4. customThe crude product was purified on silica gel column

출처 및 근거

ORD 기록
ord-a342cb291e2d42a7b6819310f85c9b58
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08876914B2

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