Hydrochloric Acid → 2-Propoxyethyl 4-Bromobenzenesulfonate

HRID 1058751Notes

Reaction equation

HRID 1058751 reaction equation
[CH2:1]([O:4][CH2:5][CH2:6][OH:7])[CH2:2][CH3:3].C(N(CC)CC)C.[Br:15][C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.Cl>ClCCl.O>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([O:7][CH2:6][CH2:5][O:4][CH2:1][CH2:2][CH3:3])(=[O:24])=[O:23])=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7396p-Bromobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 17756Glycol monopropyl ether

Product 1

HCID 227079362-Propoxyethyl 4-BromobenzenesulfonateYield 48%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-propoxy-1-ethanol (1.5 g, 14.4 mmol) and triethylamine (2.2 g, 21.6 mmol) in dichloromethane (20 mL) at 0° C. was added 4-bromobenzenesulfonyl chloride (3.86 g, 15.1 mmol) in dichloromethane (10 mL) dropwise over 30 minutes. The reaction was then warmed to room temperature and stirred for 16 hours. The mixture was then poured into water (50 mL) and acidified with 2N aqueous hydrochloric acid (15 mL). The aqueous layer was extracted with dichloromethane and the combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to give a crude residue. This was purified by column chromatography on silica gel (50 g), eluting with hexane:ethyl acetate (9:3), to give the title compound (2.2 g, 48%) as a colourless oil.

Workup

  1. extractionThe aqueous layer was extracted with dichloromethane
  2. dry with materialthe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a crude residue
  6. customThis was purified by column chromatography on silica gel (50 g)
  7. washeluting with hexane:ethyl acetate (9:3)

Sources & evidence

ORD record
ord-c89d7cc853f34728b8f8c96a8a5e393d
Source dataset
uspto-grants-2003_02
Patent number
US06518282B1

Reaction notes

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