Water → HCID 86685486, compound

HRID 1037042Notes

Reaction equation

HRID 1037042 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:12](=[O:14])[CH3:13])[CH:5]=[CH:6][C:7]=1[C:8]([OH:11])([CH3:10])[CH3:9].Cl[CH2:16][O:17][CH2:18][CH3:19].CCN(C(C)C)C(C)C.O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:12](=[O:14])[CH3:13])[CH:5]=[CH:6][C:7]=1[C:8]([O:11][CH2:16][O:17][CH2:18][CH3:19])([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 18523Chloromethyl ethyl etherHCID 81531DiisopropylethylamineHCID 86685487HCID 86685487, compound

Product 1

HCID 86685486HCID 86685486, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 1-(3-bromo-4-(2-hydroxypropan-2-yl)phenyl)ethanone (0.9 g, 3.51 mmol), (chloro-methoxy)ethane (660 mg, 7.02 mmol) and DIPEA (2.5 mL, 14.04 mmol) in DCM (20 mL) was stirred at 40° C. overnight under argon. Water (50 mL) was added and the mixture was extracted with DCM (50 mL×2). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel eluted with PE-EA (10:1) to give 1-(3-bromo-4-(2-(ethoxymeth-oxy)propan-2-yl)phenyl)ethanone (990 mg; yield 90%) as a white solid.

Workup

  1. extractionthe mixture was extracted with DCM (50 mL×2)
  2. washThe combined organic layers were washed with 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 (10:1)

Sources & evidence

ORD record
ord-f5abc8199f14469f95a0c49528b17555
Source dataset
uspto-grants-2013_10
Patent number
US08546357B2

Reaction notes

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