3-Bromophenol → 1-Bromo-3-(2,2-diethoxyethoxy)benzene

HRID 850587Notes

Reaction equation

HRID 850587 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1.[CH2:11]([O:13][CH:14]([O:17][CH2:18][CH3:19])[CH2:15]Br)[CH3:12]>CN(C=O)C>[Br:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:15][CH:14]([O:17][CH2:18][CH3:19])[O:13][CH2:11][CH3:12])[CH:5]=1

Participants

5

Reactant 3

HCID 115633-BromophenolHCID 24758Sodium hydrideHCID 74852Ethane, 2-bromo-1,1-diethoxy-

Product 1

HCID 154537651-Bromo-3-(2,2-diethoxyethoxy)benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
100 °C

Procedure

To a suspension of NaH (2.77 g, 115.6 mmol) in DMF (100 mL) at 0° C. was added a solution of 3-bromophenol 1-1 in DMF (40 mL) over 40 min. After the addition was complete, the solution was stirred for an additional 30 min. The solution was then treated with neat bromoacetaldehyde diethyl acetal (17.36 g, 115.6 mmol). The solution was heated at 100° C. for 8 h, cooled to room temperature, and extracted with Et2O (3×200 mL). The combined organic extracts were washed with 10% aq. NaOH (100 mL) and brine (100 mL), dried over MgSO4, filtered and concentrated to give 1-2 as a yellow oil. TLC Rf=0.4 (10% ethyl acetate/hexanes). 1H NMR (300 MHz, CDCl3) δ 7.19-7.05 (m, 3H), 6.85 (d, 1H), 4.81 (t, 1H, J=6.8 Hz), 3.99 (d, 2H, J=6.8 Hz), 3.71 (m, 4H), 1.22 (t, 6H, J=7.1 Hz)

Workup

  1. additionAfter the addition
  2. temperaturecooled to room temperature
  3. extractionextracted with Et2O (3×200 mL)
  4. washThe combined organic extracts were washed with 10% aq. NaOH (100 mL) and brine (100 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-84ac66542ddb43fd976dc036993eff44
Source dataset
uspto-grants-2000_01
Patent number
US06017926

Reaction notes

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