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

HRID 2416680ノート

反応式

HRID 2416680 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-bf1b8820d2a04b1586ad7f0102bdfd21
出典データセット
uspto-grants-2004_11
特許番号
US06825188B2

反応ノート

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