Hydrochloric Acid → 2-(2-Naphthyloxy)ethyl 4-Bromobenzenesulfonate

HRID 1058748Notes

Reaction equation

HRID 1058748 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH2:12][CH2:13][OH:14].C(N(CC)CC)C.[Br:22][C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1.Cl>ClCCl.O>[Br:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([O:14][CH2:13][CH2:12][O:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)(=[O:31])=[O:30])=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 71312-(2-Naphthoxy)ethanolHCID 7396p-Bromobenzenesulfonyl chloride2×HCID 8471Triethylamine

Product 1

HCID 186691322-(2-Naphthyloxy)ethyl 4-BromobenzenesulfonateYield 17.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(2-naphthyloxy)-1-ethanol (1.5 g, 7.97 mmol) and triethylamine (1.21 g, 11.95 mmol) in dichloromethane (20 mL) at 0° C. was added 4-bromobenzenesulfonyl chloride (2.12 g, 8.36 mmol) in dichloromethane (10 mL) dropwise over 30 minutes. The reaction was then warmed to room temperature and stirred for 16 hours before more 4-bromobenzenesulfonyl chloride (0.20 g, 0.80 mmol) was added and stirring was continued for 2 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 (9:2), to give the title compound (0.56 g, 17%) as a white crystalline solid.

Workup

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

Sources & evidence

ORD record
ord-2e013504b86749dbad09048931ddb810
Source dataset
uspto-grants-2003_02
Patent number
US06518282B1

Reaction notes

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