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

HRID 868718ノート

反応式

HRID 868718 の反応式
[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

参加物

5

反応物 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 2401474-Mercaptophenol

生成物 1

HCID 130526324-((2-Hydroxyethyl)thio)phenol収率 72%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

(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).

後処理

  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

出典と根拠

ORDレコード
ord-739e8ba836224e02a3ac2d1a3b3ef8dc
出典データセット
uspto-grants-2015_03
特許番号
US08968421B2

反応ノート

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