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

HRID 868718Notes

Reaction equation

HRID 868718 reaction equation
[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

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 2401474-Mercaptophenol

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(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).

Workup

  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

Sources & evidence

ORD record
ord-739e8ba836224e02a3ac2d1a3b3ef8dc
Source dataset
uspto-grants-2015_03
Patent number
US08968421B2

Reaction notes

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