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

HRID 1433154Notes

Reaction equation

HRID 1433154 reaction equation
[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

Participants

4

Reactant 2

HCID 17977687Phenyltrimethylammonium bromide dibromideHCID 69059816HCID 69059816, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-250d864f162b4a98bbf6901e7f22625f
Source dataset
uspto-grants-2009_11
Patent number
US07612201B2

Reaction notes

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