Cesium carbonate → HCID 58531600, compound

HRID 1889716Notes

Reaction equation

HRID 1889716 reaction equation
[C:1]1([CH2:7][CH2:8][SH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:11][C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=1)[C:15]([O:17][CH3:18])=[O:16].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C.O>[CH2:8]([S:9][CH2:11][C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=1)[C:15]([O:17][CH3:18])=[O:16])[CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 781262-PhenylethanethiolHCID 517981Methyl 3-(bromomethyl)benzoate

Product 1

HCID 58531600HCID 58531600, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of phenylethyl mercaptan (0.66 g, 4.80 mmol) and methyl 3-(bromomethyl)benzoate (1.0 g, 4.37 mmol) in DMF (10 mL) was added Cs2CO3 (2.84 g, 8.73 mmol). The suspension was stirred at rt for 3 h. The reaction mixture was then diluted with ethyl acetate and water. The organic layer was separated, washed with brine three times, dried over MgSO4. The filtrate was concentrated in vacuo to give a light yellow oil. The crude product was purified by flash chromatography on silica gel eluting with 30% ethyl acetate in hexane to give the desired product (1.2 g, 96%) as a colorless oil. 1H NMR (CDCl3) δ 8.00 (s, 1H), 7.96-7.94 (m, 1H), 7.55-7.53 (m, 1H), 7.42 (t, J=8.0 Hz, 1H), 7.33-7.28 (m, 2H), 7.25-7.17 (m, 3H), 3.95 (s, 3H), 3.76 (s, 2H), 2.89-2.85 (m, 2H), 2.69-2.65 (m, 2H). MS (ESI): 287.1 (M+H)−.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine three times
  3. dry with materialdried over MgSO4
  4. concentrationThe filtrate was concentrated in vacuo
  5. customto give a light yellow oil
  6. customThe crude product was purified by flash chromatography on silica gel eluting with 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-d2c5b17f68da4ca78e4a192165ad3530
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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