2-Bromo-1,1-dimethoxyethane → HCID 21071775, compound

HRID 1372152Notes

Reaction equation

HRID 1372152 reaction equation
[O-]CC.[Na+].[Br:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][C:7]=1[OH:13].Br[CH2:15][CH:16]([O:19][CH3:20])[O:17][CH3:18]>C(O)C>[Br:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][C:7]=1[O:13][CH2:15][CH:16]([O:19][CH3:20])[O:17][CH3:18]

Participants

5

Reactant 3

HCID 816722-Bromo-1,1-dimethoxyethaneHCID 2286382-Bromo-5-methylphenolHCID 2723922Sodium ethoxide

Product 1

HCID 21071775HCID 21071775, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of anhydrous ethanol (40 ml), sodium ethoxide (31.7 ml 21% wt., 86.94 mmol) and 2-bromo-5-methylphenol (Gewali, Mohan B.; Ronald, Bruce P. J. Org. Chem. 1980, 45, 2224–2229) (16.25 g, 86.94 mmol) was added 2-bromo-1,1-dimethoxy ethane (16.17 g, 95.64 mmol). The solution was heated to reflux overnight, reduced under vacuum and partitioned between water and ether. The aqueous layer was extracted with ether and the organics were passed through a silica plug and concentrated to afford 8.71 g (36%) of desired product as a pale yellow oil: 1H NMR (400 MHz, DMSO-d6): δ 2.19 (3H, s), 3.33 (6H, s), 3.96 (2H, d, J=5.1 Hz), 4.64 (1H, t, J=5.1 Hz), 6.98 (1H, d, J=8.5 Hz), 7.08 (1H, dd, J=8.4 Hz, 1.5 Hz), 7.35 (1H, d, J=1.7 Hz).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux overnight
  3. custompartitioned between water and ether
  4. extractionThe aqueous layer was extracted with ether
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d0a7ad09265c48f8bb1cd0ab1c70de94
Source dataset
uspto-grants-2007_01
Patent number
US07157491B2

Reaction notes

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