p-Xylyl bromide → HCID 66918677, compound

HRID 1367546Notes

Reaction equation

HRID 1367546 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:9][C@H:8]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])(=[O:12])=[O:11])[CH2:7][C@@H:6]1[OH:20])=[O:4].Br[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=1>C(Cl)Cl.[Ag-]=O>[CH3:1][O:2][C:3]([C@H:5]1[CH2:9][C@H:8]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])(=[O:11])=[O:12])[CH2:7][C@@H:6]1[O:20][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=1)=[O:4]

Participants

5

Reactant 2

HCID 7721p-Xylyl bromideHCID 66918607HCID 66918607, compound

Product 1

HCID 66918677HCID 66918677, compoundYield 59.3%

Reagents, catalysts & solvents 2

HCID 178418778HCID 178418778, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of (1R,2R,4R) and (1S,2S,4S)-4-(2-chloro-benzenesulfonyl)-2-hydroxy-cyclopentanecarboxylic acid methyl ester (80 mg, 0.251 mmol, example 48, step 5), 1-(bromomethyl)-4-methylbenzene (232 mg, 1.25 mmol) and silver(I) oxide (116 mg, 0.502 mmol) in DCM (2 ml) was stirred at room temperature for 60 h. The reaction mixture was filtered through a pad of Celite, the pad was washed with DCM and the filtrate was evaporated. The remaining grey oil was purified by silica gel chromatography (heptane/EtOAc 80:20-70:30) to obtain the title compound (63 mg, 56%) as colorless oil. MS (EI): 423.1 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. washthe pad was washed with DCM
  3. customthe filtrate was evaporated
  4. customThe remaining grey oil was purified by silica gel chromatography (heptane/EtOAc 80:20-70:30)

Sources & evidence

ORD record
ord-fb2c74bd01a64c1c9be943a5e408eeb8
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

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