Phenyltrimethylammonium bromide dibromide → N-[3-benzyloxy-4-(2,2-dibromo-acetyl)phenyl]-acetamide

HRID 1433154ノート

反応式

HRID 1433154 の反応式
[Br-:1].[Br-:2].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.[C:34]([C:37]1[CH:42]=[CH:41][C:40]([NH:43][C:44](=[O:46])[CH3:45])=[CH:39][C:38]=1[O:47][CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)(=[O:36])[CH3:35]>C1COCC1>[CH2:48]([O:47][C:38]1[CH:39]=[C:40]([NH:43][C:44](=[O:46])[CH3:45])[CH:41]=[CH:42][C:37]=1[C:34](=[O:36])[CH:35]([Br:2])[Br:1])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1

参加物

4

反応物 2

HCID 17977687Phenyltrimethylammonium bromide dibromideHCID 69059816HCID 69059816、化合物

生成物 1

HCID 85978776N-[3-benzyloxy-4-(2,2-dibromo-acetyl)phenyl]-acetamide収率 100%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Phenyltrimethylammonium tribromide (102 mg, 0.272 mmol) was added to a solution of N-(4-acetyl-3-benzyloxy-phenyl)-acetamide (35 mg, 0.124 mmol) in THF (3.5 mL), and stirred at room temperature for 2 hours. The mixture was partitioned between water (25 mL) and EtOAc (25 mL), the layers separated and the organic layer dried (MgSO4). The solvents were removed in vacuo to give crude N-[3-benzyloxy-4-(2,2-dibromo-acetyl)-phenyl]-acetamide (54 mg, 100%) as a pale brown solid; δH (CDCl3) 7.92 (1H, br s), 7.85 (1H, d, J=8.5 Hz), 7.55 (1H, br s), 7.50-7.35 (5H, m), 7.09 (1H, s), 6.78 (1H, dd, J=8.5, 1.9 Hz), 5.20 (2H, s), 2.21 (3H, s); LCMS retention time 2.65 min, M+H+ 440.1/442.1/444.1. The mixture was used crude in the next step.

後処理

  1. customThe mixture was partitioned between water (25 mL) and EtOAc (25 mL)
  2. customthe layers separated
  3. dry with materialthe organic layer dried (MgSO4)
  4. customThe solvents were removed in vacuo

出典と根拠

ORDレコード
ord-250d864f162b4a98bbf6901e7f22625f
出典データセット
uspto-grants-2009_11
特許番号
US07612201B2

反応ノート

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