4-Isopropylthiophenol → HCID 20985432, compound

HRID 1518205Notes

Reaction equation

HRID 1518205 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].Br[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([OH:22])=[O:21])=[CH:15][CH:14]=1>CN(C)C=O>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([CH2:19][C:20]([OH:22])=[O:21])=[CH:17][CH:18]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 5212514-IsopropylthiophenolHCID 45190564-(Bromomethyl)phenylacetic acid

Product 1

HCID 20985432HCID 20985432, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 4-(isopropyl)thiophenol (10 g, 65.68 mmol) in N,N-dimethylformamide (200 ml) sodium hydride (3.15 g, 131.35 mmol) was added. The exothermic reaction was allowed to cool down to room temperature. At 15° C. a solution of (4-bromomethyl-phenyl)-acetic acid (15.04 g, 65.68 mmol) in N,N-dimethylformamide (100 ml) was added. After stirring the reaction mixture at room temperature for 16 h the mixture was concentrated, diluted with water, and adjusted to pH=2 by adding HCl (2N). The aqueous phase was extracted three times with ethyl acetate. The combined organic layers were dried over MgSO4, filtered, and the solvent evaporated under reduced pressure to give the product as a yellow oil (19.5 g, 99%).

Workup

  1. customThe exothermic reaction
  2. concentrationwas concentrated
  3. additiondiluted with water
  4. additionby adding HCl (2N)
  5. extractionThe aqueous phase was extracted three times with ethyl acetate
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-197bed3c647744828ab5518f529ad3f3
Source dataset
uspto-grants-2012_07
Patent number
US08232426B2

Reaction notes

Loading…