Water → Ethyl 4-(4-bromophenyl)-2-methanesulfonyl-2-methylbutanoate

HRID 533499Notes

Reaction equation

HRID 533499 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9]I)=[CH:4][CH:3]=1.[CH2:11]([O:13][C:14](=[O:21])[CH:15]([S:17]([CH3:20])(=[O:19])=[O:18])[CH3:16])[CH3:12].C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:15]([CH3:16])([S:17]([CH3:20])(=[O:18])=[O:19])[C:14]([O:13][CH2:11][CH3:12])=[O:21])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 10511577Ethyl 2-(methylsulfonyl)propanoateHCID 197022221-Bromo-4-(2-iodoethyl)benzene

Product 1

HCID 56950323Ethyl 4-(4-bromophenyl)-2-methanesulfonyl-2-methylbutanoateYield 72.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 1-bromo-4-(2-iodo-ethyl)-benzene (25.0 g, 80 mmol) and (+/−)-2-methanesulfonyl-propionic acid ethyl ester (15.9 g, 88.4 mmol) in DMF (100 mL) with solid Cs2CO3 (52.4 g, 161 mmol) was stirred overnight at room temperature. After 16 hours the reaction was poured into water (500 mL). The resulting suspension was stirred for 2 h. The mixture was extracted with diethylether (2×). The organic layers were combined and washed with water then brine, dried (Na2SO4) and concentrated in vacuo. Purification by flash column chromatography on silica gel (hexanes/ethyl acetate 9:1-8:2) afforded the title compound as a white solid (21.0 g, 72%). 1HNMR (400 MHz, CHLOROFORM-d) δ ppm 1.35 (t, J=7.22 Hz, 3H) 1.70 (s, 3H) 2.14-2.24 (m, 1H) 2.42-2.55 (m, 2H) 2.68-2.78 (m, 1H) 3.04 (s, 3H) 4.25-4.31 (m, 2H) 7.07 (d, J=8.20 Hz, 2H) 7.43 (d, J=8.20 Hz, 2H)

Workup

  1. stirringThe resulting suspension was stirred for 2 h
  2. extractionThe mixture was extracted with diethylether (2×)
  3. washwashed with water
  4. dry with materialbrine, dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customPurification by flash column chromatography on silica gel (hexanes/ethyl acetate 9:1-8:2)

Sources & evidence

ORD record
ord-513ae7e49e0a4b48b63ef252ddc4993d
Source dataset
uspto-grants-2014_10
Patent number
US08853258B2

Reaction notes

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