2-Bromo-5-methoxybenzyl bromide → 3-Bis(tert-butoxycarbonyl)aminomethyl-4-bromoanisole

HRID 2416680노트

반응식

HRID 2416680 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH2:10]Br.[NH:12]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].[K]>CN(C)C=O>[C:23]([O:22][C:20]([N:12]([CH2:10][C:3]1[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=1[Br:1])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:21])([CH3:26])([CH3:25])[CH3:24]

참가 물질

4

반응물 2

HCID 35259512-Bromo-5-methoxybenzyl bromideHCID 86222903Imidodicarbonic acid, bis(1,1-dimethylethyl) ester, potassium salt

생성물 1

HCID 226321523-Bis(tert-butoxycarbonyl)aminomethyl-4-bromoanisole수율 42%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 4-bromo-3-bromomethylanisole (24 g, 86 mmol) and potassium di-tert-butyl iminodicarboxylate (24 g, 94 mmol) in dimethylformamide (200 mL) was stirred under argon at room temperature for 18 hr. The reaction was then concentrated under vacuum and the residue was partitioned between ethyl acetate and water. The organic phase was washed with water and brine, dried(MgSO4), and concentrated. The residue was recrystallized from hexane to give the title compound (15 g, 42%) as a white solid: 1H NMR (CDCl3) δ 7.40 (d, J=8.6 Hz, 1 H), 6.68 (m, 2 H), 4.81(s, 2 H), 3.74 (s, 3 H) 1.44 (s, 18 H).

후처리

  1. concentrationThe reaction was then concentrated under vacuum
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe organic phase was washed with water and brine, dried(MgSO4)
  4. concentrationconcentrated
  5. customThe residue was recrystallized from hexane

출처 및 근거

ORD 기록
ord-bf1b8820d2a04b1586ad7f0102bdfd21
출처 데이터셋
uspto-grants-2004_11
특허 번호
US06825188B2

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