4-Methoxybenzyl alcohol → 4-Methoxybenzyl 2-bromoacetate

HRID 1378717

반응식

HRID 1378717 반응식
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][OH:10])=[CH:7][CH:8]=1.C(N(CC)CC)C.[Br:18][CH2:19][C:20](Br)=[O:21]>C(Cl)Cl>[Br:18][CH2:19][C:20]([O:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:21]

참가 물질

5

반응물 3

HCID 77384-Methoxybenzyl alcoholHCID 8471TriethylamineHCID 61147Bromoacetyl bromide

생성물 1

HCID 132332344-Methoxybenzyl 2-bromoacetate수율 93%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a -78 ° C. solution of p-methoxybenzyl alcohol (6.91 g, 50 mmol) and triethylamine (6.95 mL, 50 mmol) in anhydrous CH2Cl2 (50 mL) was added a solution of bromoacetyl bromide (10.1 g, 50 mmol) in CH2Cl2 at -78° C. under nitrogen, over a period of 10 min. The cooling bath was removed, and the reaction mixture was stirred for 2 h. The mixture was washed with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated to provide 12 g (93% yield) of p-methoxybenzyl bromoacetate as a dark colored oil which was used in the next reaction without purification. A portion was purified by column chromatography on silica gel (elution with 20% ethyl acetate/hexanes) to give a clear, colorless oil. 1H NMR (300 MHz, CDCl3 ) δ3.79 (s, 3 H), 3.83 (s, 2 H), 5.12 (s, 2 H), 6.87 (m, 2 H), and 7.30 (m, 2 H); IR (film) 1738 cm-1 ; MS (ESI/NH4OAc) M+NH4+ =276.

후처리

  1. customThe cooling bath was removed
  2. washThe mixture was washed with water and saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e54384815ce947099ae8325f54cc7bb8
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05668290

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