Benzyl Bromide → HCID 54165552, compound

HRID 1531021Notes

Reaction equation

HRID 1531021 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH:5]([S:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)[CH3:6])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1COCC1>[CH2:1]([O:3][C:4](=[O:16])[C:5]([S:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=1)([CH3:6])[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH3:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 2733832Lithium HexamethyldisilazideHCID 12052028HCID 12052028, compound

Product 1

HCID 54165552HCID 54165552, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 2-(4-methoxy-phenylsulfanyl)-propionic acid ethyl ester (2.44 g, 10 mmol), in THF (100 ml) at −4° C., lithium bis(trimethylsilyl)amide (1 M solution, 15 ml, 15 mmol) was added slowly. The orange colored reaction mixture was stirred at room temperature for 15 minutes and then it was cooled to 0° C. at which time it was stirred for an additional hour. The temperature of the mixture was again brought to −40° C. and benzylbromide (1.72 gm, 10 mmol) was added dropwise in THF. The reaction was warmed to room temperature and stirred overnight before it was quenched with ice water, extracted with chloroform and washed with water. The organic layer was dried over MgSO4, filtered and concentrated and chromatographed on a silica-gel column with 10% ethyl acetate:hexane to afford 2-(4-methoxy-phenylsulfanyl)-2-methyl-3-phenyl-propionic acid ethyl ester as a colorless oil. Yield: 860 mg, (26%); MS: 331 (M+H)+.

Workup

  1. temperatureit was cooled to 0° C. at which time it
  2. stirringwas stirred for an additional hour
  3. customwas again brought to −40° C.
  4. temperatureThe reaction was warmed to room temperature
  5. stirringstirred overnight before it
  6. customwas quenched with ice water
  7. extractionextracted with chloroform
  8. washwashed with water
  9. dry with materialThe organic layer was dried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customchromatographed on a silica-gel column with 10% ethyl acetate

Sources & evidence

ORD record
ord-9ecd986d12d34e7eab79bdd2c2be2794
Source dataset
uspto-grants-2001_03
Patent number
US06197791B1

Reaction notes

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