Imidazole → 1-(Bromomethyl)-3-ethylbenzene

HRID 2045839

반응식

HRID 2045839 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 220036561-(Bromomethyl)-3-ethylbenzene수율 87.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-52d018b5833d4dabba78049eae925ad8
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08592413B2

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