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

HRID 9632

反応式

HRID 9632 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a1c31f05a7504c58b2c582a15b337fab
出典データセット
uspto-grants-2006_08
特許番号
US07091237B2

関連ノート

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