Water → HCID 14606696, compound

HRID 1097826Notes

Reaction equation

HRID 1097826 reaction equation
N12CCN(CC1)CC2.[Br:9][C:10]1[CH:18]=[CH:17][C:13]([CH2:14][CH2:15][OH:16])=[CH:12][CH:11]=1.[S:19](Cl)([C:22]1[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=1)(=[O:21])=[O:20].O>ClCCl>[CH3:26][C:25]1[CH:27]=[CH:28][C:22]([S:19]([O:16][CH2:15][CH2:14][C:13]2[CH:17]=[CH:18][C:10]([Br:9])=[CH:11][CH:12]=2)(=[O:21])=[O:20])=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 9237DabcoHCID 728512-(4-Bromophenyl)ethanol

Product 1

HCID 14606696HCID 14606696, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

1,4-Diazabicyclo[2.2.2]octane (5.61 g, 0.050 mol) and 4-bromophenethyl alcohol (5.0 g, 0.025 mol) were combined in dichloromethane (100 mL). The resulting mixture was cooled to 0° C. in an ice bath and a solution of tosyl chloride (5.67 g, 0.029 mol) in dichloromethane (50 mL) was added via an addition funnel over 15 min. After stirring for about 1 h at 0° C., water (30 mL) was added and stirring was continued for another 30 min. The aqeuous layer was then separated and discarded. The organic layer was dried (NaSO2), filtered, and concentrated under reduced pressure to give the title compound as a white solid.

Workup

  1. stirringstirring
  2. waitwas continued for another 30 min
  3. customThe aqeuous layer was then separated
  4. dry with materialThe organic layer was dried (NaSO2)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5bc04f71f7bd4c1ca5e6e49f553b3970
Source dataset
uspto-grants-2012_03
Patent number
US08143277B2

Reaction notes

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