Chloromethyl Methyl Ether → 2-Bromo-1-(1-(methoxymethoxy)cyclopentyl)-4-methylbenzene

HRID 1037032Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1037032
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1([OH:14])[CH2:13][CH2:12][CH2:11][CH2:10]1.CCN(C(C)C)C(C)C.[CH2:24](Cl)[O:25][CH3:26].[NH4+].[Cl-]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1([O:14][CH2:24][O:25][CH3:26])[CH2:13][CH2:12][CH2:11][CH2:10]1

Komponenten

6

Edukt 4

HCID 7864Chloromethyl Methyl EtherHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 726983321-(2-Bromo-4-methylphenyl)cyclopentanol

Produkt 1

HCID 866854782-Bromo-1-(1-(methoxymethoxy)cyclopentyl)-4-methylbenzeneAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirring solution of 1-(2-bromo-4-methylphenyl)cyclopentanol (4.2 g, 16.5 mmol) in DCM (40 mL) at rt were successively added DIPEA (11 mL, 66 mmol) and MOMCl (2.5 mL, 33 mmol) over a 10 min period. The solution was stirred for 11 h at rt, and afterwards a NH4Cl-saturated aqueous solution (40 mL) was added. The aqueous phase was segregated, and the organic one was washed with water (30 mL), brine (30 mL), dried with anhydrous Na2SO4, filtered, and concentrated to give pure 2-bromo-1-(1-(methoxymethoxy)cyclopentyl)-4-methylbenzene (4.0 g, yield 81%).

Aufarbeitung

  1. customat rt
  2. customover a 10 min
  3. washthe organic one was washed with water (30 mL), brine (30 mL)
  4. dry with materialdried with anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-1b689cb9a58f4792942b95ba94c37e84
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546357B2

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