4-Toluenesulfonyl chloride → HCID 14606696, compound

HRID 2362670Notes

Reaction equation

HRID 2362670 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.ClCCl.C(OCC)(=O)C>[CH3:21][C:11]1[CH:16]=[CH:15][C:14]([S:17]([O:10][CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)(=[O:19])=[O:18])=[CH:13][CH:12]=1

Participants

7

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 728512-(4-Bromophenyl)ethanol

Product 1

HCID 14606696HCID 14606696, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(4-bromophenyl)ethanol (3.48 mL, 24.87 mmol), p-toluenesulfonyl chloride (5.69 g, 29.8 mmol), and 4-(dimethylamino)pyridine (0.304 g, 2.487 mmol) in anhydrous dichloromethane (70 mL) was treated with triethylamine (6.93 mL, 49.7 mmol). The reaction stirred for 16 hours at ambient temperature. The reaction was diluted with ethyl acetate and washed with water and brine. The organic layer dried with sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with a gradient of 10 to 20% ethyl acetate in hexanes, to give the title compound. MS ESI(+) m/z 356.9 [M+H]+.

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography on silica gel
  6. washeluting with a gradient of 10 to 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-e58b70cca885453f9cb5b3071766e49d
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

Loading…