Cesium carbonate → Ethyl 4-(3-bromophenoxy)butanoate

HRID 1506415Notes

Reaction equation

HRID 1506415 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 115633-BromophenolHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 22407915Ethyl 4-(3-bromophenoxy)butanoateYield 99.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-bromophenol (2 g, 11.56 mmol) in dimethylformamide (10 mL) was added sequentially cesium carbonate (11.30 g, 34.7 mmol) and ethyl 4-bromobutanoate (1.66 mL, 11.6 mmol) at room temperature. The heterogeneous reaction mixture was stirred at room temperature for 2.5 h. The reaction mixture was partitioned between ether (75 mL) and water (50 mL). The ether layer was collected, washed with brine (50 mL), dried over sodium sulfate, and concentrated to yield ethyl 4-(3-bromophenoxy)butanoate (3.3 g, 11.5 mmol, 99% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.25-1.29 (m, 3H), 2.07-2.15 (m, 2H), 2.48-2.54 (m, 2H), 3.99 (t, J=6.16 Hz, 2H), 4.13-4.15 (m, 1H), 4.16-4.19 (m, 1H), 6.80-6.84 (m, 1H), 7.05 (t, J=1.98 Hz, 1H), 7.06-7.09 (m, 1H), and 7.11-7.16 (m, 1H).

Workup

  1. customThe reaction mixture was partitioned between ether (75 mL) and water (50 mL)
  2. customThe ether layer was collected
  3. washwashed with brine (50 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9caa65be00ab45f28933f091a6f424b3
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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