Imidazole → 1-(Bromomethyl)-3-ethylbenzene

HRID 2045839

反応式

HRID 2045839 の反応式
[Br:1]Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[CH2:27]([C:29]1[CH:30]=[C:31]([CH2:35]O)[CH:32]=[CH:33][CH:34]=1)[CH3:28]>C(Cl)Cl>[Br:1][CH2:35][C:31]1[CH:32]=[CH:33][CH:34]=[C:29]([CH2:27][CH3:28])[CH:30]=1

参加物

6

反応物 4

HCID 795ImidazoleHCID 11776TriphenylphosphineHCID 24408BromineHCID 104659(3-Ethylphenyl)methanol

生成物 1

HCID 220036561-(Bromomethyl)-3-ethylbenzene収率 87.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Bromine (0.21 mL, 4.08 mmol) was added dropwise to a solution of triphenylphosphine (1.08 g, 4.12 mmol) and imidazole (280 mg, 4.11 mmol) in CH2Cl2 (13.5 mL) at 0° C. The mixture was allowed to warm to room temperature and then a solution of (3-ethylphenyl)methanol (˜3.05 mmol) in CH2Cl2 (3.5 mL) was added. After 1 h, the mixture was diluted with hexanes and filtered through celite, washing with excess hexanes. The filtrate was concentrated in vacuo. Purification of the crude residue by chromatography on silica gel (hexanes→10% EtOAc/hexanes, gradient) afforded 530 mg (87% over two steps) of 1-(bromomethyl)-3-ethylbenzene.

後処理

  1. filtrationfiltered through celite
  2. washwashing with excess hexanes
  3. concentrationThe filtrate was concentrated in vacuo
  4. customPurification of the crude residue by chromatography on silica gel (hexanes→10% EtOAc/hexanes, gradient)

出典と根拠

ORDレコード
ord-52d018b5833d4dabba78049eae925ad8
出典データセット
uspto-grants-2013_11
特許番号
US08592413B2

関連ノート

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