Water → HCID 14852816, compound

HRID 1073412Notes

Reaction equation

HRID 1073412 reaction equation
CC(C)([O-])C.[K+].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([SH:15])=[CH:11][CH:10]=1.Br[CH:17]([CH2:19][CH3:20])[CH3:18].O>CN(C=O)C>[CH3:18][CH:17]([S:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][CH3:7])=[CH:10][CH:11]=1)[CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 65542-BromobutaneHCID 127654-MethoxybenzenethiolHCID 23665647Potassium tert-butoxide

Product 1

HCID 14852816HCID 14852816, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Potassium t-butoxide (30.6 g, 275.0 mmol) is added to a solution of 4-methoxybenzenethiol (30.0 ml, 250.0 mmol) in 250 ml of DMF. The mixture is heated at 80° until homogeneous, after which 2-bromobutane (30.0 ml, 275.0 mmol) in 30 ml of DMF is added dropwise over approx. 30 min. The mixture is stirred at 60° overnight after which it is cooled and is then poured into water and the aqueous phase is extracted with ether (3×). The combined ether extracts are washed with water, with 5% sodium hydroxide, with water and with brine, dried, and the solvent removed to give 4-(1-methylpropylthio)anisole.

Workup

  1. additionis added dropwise over approx. 30 min
  2. temperatureis cooled
  3. extractionthe aqueous phase is extracted with ether (3×)
  4. washThe combined ether extracts are washed with water, with 5% sodium hydroxide, with water and with brine
  5. customdried
  6. customthe solvent removed

Sources & evidence

ORD record
ord-ec7f47f2dc3b4a23a4c827b8ee38676f
Source dataset
uspto-grants-1990_11
Patent number
US04968829

Reaction notes

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