Chloromethyl Methyl Ether → HCID 68193206, compound

HRID 1626792Notes

Reaction equation

HRID 1626792 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([CH3:18])([CH3:17])[CH2:15][OH:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:19][O:20][CH2:21]Cl.C(N(CC)C(C)C)(C)C>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([CH3:18])([CH3:17])[CH2:15][O:16][CH2:19][O:20][CH3:21])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 68193215HCID 68193215, compound

Product 1

HCID 68193206HCID 68193206, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(4′-Bromobiphenyl-4-yl)-2-methylpropan-1-ol (5.0 g, 16 mmol) was dissolved in toluene (40 mL), and chloromethyl methyl ether (2.5 mL, 33 mmol) and N,N-diisopropylethylamine (3.6 mL, 21 mmol) were added, followed by stirring at room temperature for 17 hours. After the reaction solution was diluted with ethyl acetate, the organic layer was washed with water. After the solvent was distilled off under reduced pressure, the resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate), and a fraction corresponding to the Rf value=0.45 (hexane/ethyl acetate=10/1) by thin layer chromatography was concentrated under reduced pressure to afford the title compound (5.8 g, 16 mmol) as a white solid (yield 100%).

Workup

  1. washthe organic layer was washed with water
  2. distillationAfter the solvent was distilled off under reduced pressure
  3. customthe resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate)
  4. concentrationa fraction corresponding to the Rf value=0.45 (hexane/ethyl acetate=10/1) by thin layer chromatography was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9592084ff2b249c080b6efea4de386bf
Source dataset
uspto-grants-2014_07
Patent number
US08785462B2

Reaction notes

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