Sodium Hydroxide → HCID 59371325, compound

HRID 2095341Notes

Reaction equation

HRID 2095341 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][OH:10])[CH:5]=[CH:6][CH:7]=1.Br[CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH2:8][CH2:9][O:10][CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 27340902-(3-Bromophenyl)ethan-1-ol

Product 1

HCID 59371325HCID 59371325, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent

Procedure

To a mixture of 2-(3-bromophenyl)ethanol (3.40 g, 16.9 mmol), tert-butyl 2-bromoacetate (26.0 g, 133 mmol, 8.0 equiv.), tetra-n-butylammonium hydrogen sulfate (4.52 g, 13.3 mmol, 0.80 equiv.), and 84 mL of toluene was added 267 mL of 5N aqueous NaOH solution. The reaction mixture was stirred at room temperature for 3 h. The aqueous layer was then extracted with four portions of EtOAc, dried (MgSO4), and evaporated. The residue was purified by CC on silica gel with EtOAc/petroleum ether 1:40 to afford the title compound (4.8 g, 90%) as a colorless oil. 1H NMR (CDCl3, 300 MHz) δ 7.42 (s, 1H), 7.35-7.39 (m, 1H), 7.18-7.20 (m, 2H), 3.98 (s, 2H), 3.76 (t, 2H, J=6.9 Hz), 2.94 (t, 2H, J=7.2 Hz), 1.50 (s, 9H).

Workup

  1. extractionThe aqueous layer was then extracted with four portions of EtOAc
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe residue was purified by CC on silica gel with EtOAc/petroleum ether 1:40

Sources & evidence

ORD record
ord-5c3c5e22c2694c3da5daf56249227ffa
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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