Carbon tetrabromide → Ethyl(2E)-3-[4-(bromomethyl)-2-methylphenyl]prop-2-enoate

HRID 9632

Reaktionsgleichung

Reaktionsgleichung von HRID 9632
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]([CH3:16])[CH:4]=1.C(Br)(Br)(Br)[Br:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.ClCCl.O>ClCCl>[Br:18][CH2:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]([CH3:16])[CH:4]=1

Komponenten

6

Edukt 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 21908982Water methylene chlorideHCID 21986347ethyl(2E)-3-[4-(hydroxymethyl)-2-methylphenyl]prop-2-enoate2×

Produkt 1

HCID 21986333Ethyl(2E)-3-[4-(bromomethyl)-2-methylphenyl]prop-2-enoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of ethyl(2E)-3-[4-(hydroxymethyl)-2-methylphenyl]prop-2-enoate (intermediate 19, 1.389 g) in dry dichloromethane (40 ml) was cooled to 0° C. and treated with carbon tetrabromide (2.3 g) followed by, in small portions, triphenylphosphine (1.82 g). The resulting solution was stirred thus overnight, then poured into dichloromethane/water and the organic phase separated and washed with more water, brine and dried over sodium sulfate then evaporated in vacuo. The isolated product was further purified by flash column chromatography using cyclohexane:ethyl acetate (9:1) as an eluent which gave the title compound as a white solid.

Aufarbeitung

  1. customthe organic phase separated
  2. washwashed with more water, brine
  3. dry with materialdried over sodium sulfate
  4. customthen evaporated in vacuo
  5. customThe isolated product was further purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a1c31f05a7504c58b2c582a15b337fab
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091237B2

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