Water → HCID 86685517, compound

HRID 1037073Notes

Reaction equation

HRID 1037073 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1C(O)(C)C.Cl[CH2:14][O:15][CH2:16][CH3:17].CCN([CH:24]([CH3:26])[CH3:25])C(C)C.[OH2:27]>C(Cl)Cl>[Br:1][C:2]1([C:24]([O:27][CH2:14][O:15][CH2:16][CH3:17])([CH3:25])[CH3:26])[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 18523Chloromethyl ethyl etherHCID 81531DiisopropylethylamineHCID 84692410HCID 84692410, compound

Product 1

HCID 86685517HCID 86685517, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 2-(2-bromo-4-methylphenyl)propan-2-ol (19.2 g, 83.8 mmol) in DCM (100 mL) was added (chloromethoxy)ethane (15.85 g, 168 mmol) followed by addition of DIPEA (32.44 g, 251 mmol). The reaction mixture was stirred at 40° C. for 14 h. Water (200 mL) was added and the mixture was extracted three times with DCM. The combined extracts were washed with water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel eluted with PE-EA (20:1) to give compound 2-bromo-2-(2-(ethoxymethoxy)propan-2-yl)-4-methylbenzene (21.8 g yield 91%) as yellow oil. 1H NMR (500 MHz, CDCl3): δ 7.38 (s, 1 H), 7.28 (d, J=8.0 Hz, 1 H), 7.00 (d, J=8.0 Hz, 1H), 4.57 (s, 2 H), 3.58 (q, J=7.0 Hz, 2 H), 2.22 (s, 3H), 1.67 (s, 6H), 1.11 (t, J=7.0 Hz, 3 H) ppm.

Workup

  1. extractionthe mixture was extracted three times with DCM
  2. washThe combined extracts were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography over silica gel
  7. washeluted with PE-EA (20:1)

Sources & evidence

ORD record
ord-f36aaed666ac4cdf8be799f64ca2ff94
Source dataset
uspto-grants-2013_10
Patent number
US08546357B2

Reaction notes

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