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

HRID 1433154노트

반응식

HRID 1433154 반응식
[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

참가 물질

4

반응물 2

HCID 17977687Phenyltrimethylammonium bromide dibromideHCID 69059816HCID 69059816, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-250d864f162b4a98bbf6901e7f22625f
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612201B2

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