Water → HCID 14852816, compound

HRID 2309830Notes

Reaction equation

HRID 2309830 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 (3X). 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. temperatureafter which it is cooled
  3. extractionthe aqueous phase is extracted with ether (3X)
  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-3f75b830a4e3449989812060171fd91c
Source dataset
uspto-grants-1987_09
Patent number
US04697033

Reaction notes

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