2-Bromoethanol → 2-(2-Bromo-5-chloro-4-(4-ethylbenzyl)phenoxy)ethanol

HRID 1175318Notes

Reaction equation

HRID 1175318 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[CH:11][CH:10]=2)[C:5]([Cl:17])=[CH:4][C:3]=1[OH:18].[H-].[Na+].Br[CH2:22][CH2:23][OH:24]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[CH:11][CH:10]=2)[C:5]([Cl:17])=[CH:4][C:3]=1[O:18][CH2:22][CH2:23][OH:24]

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 24758Sodium hydrideHCID 59557707HCID 59557707, compound

Product 1

HCID 595577142-(2-Bromo-5-chloro-4-(4-ethylbenzyl)phenoxy)ethanolYield 81.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-bromo-5-chloro-4-(4-ethylbenzyl)phenol (AT) (3.26 g, 10 mmol) in anhydrous DMF (15 mL), NaH (0.72 g, 30 mmol) was added in portions. The reaction mixture was stirred for 2 h at room temperature, and then 2-bromoethanol (3.75 g, 30 mmol) was added dropwise, and the reaction mixture was heated to 45° C. overnight. TLC showed the reaction was complete. The reaction was quenched with the saturated NH4Cl, the mixture was extracted with EtOAc, and then washed with water and brine. After drying with anhydrous Na2SO4 the organic portion was filtered and concentrated. The residue was purified by flash chromatography to give AU as an oil (3.00 g, yield 81%). 1H-NMR (CDCl3, 300 MHz) δ 7.32 (s, 1H), 7.13 (m, 4H), 6.94 (s, 1H), 4.11 (m, 2H), 3.57-3.99 (m, 4H), 2.64 (q, J=7.5 Hz, 2H), 1.22 (t, J=7.5 Hz, 3H).

Workup

  1. temperaturethe reaction mixture was heated to 45° C. overnight
  2. customThe reaction was quenched with the saturated NH4Cl
  3. extractionthe mixture was extracted with EtOAc
  4. washwashed with water and brine
  5. dry with materialAfter drying with anhydrous Na2SO4 the organic portion
  6. filtrationwas filtered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-3578ac6069ab4fd4a88aa62fc5fc440f
Source dataset
uspto-grants-2010_11
Patent number
US07838498B2

Reaction notes

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