Water → HCID 58966526, compound

HRID 390754Notes

Reaction equation

HRID 390754 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:4]=[C:5]([CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:22]=1)[CH2:6][NH:7][CH2:8][C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:10]=1[Br:19].C([O-])(=O)C.[Na+].[N:34]#[C:35]Br.O>C(O)C>[Br:19][C:10]1[CH:11]=[CH:12][C:13]([C:15]([F:16])([F:17])[F:18])=[CH:14][C:9]=1[CH2:8][N:7]([CH2:6][C:5]1[CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:22]=[C:3]([C:2]([F:27])([F:1])[F:28])[CH:4]=1)[C:35]#[N:34]

Participants

6

Reactant 4

HCID 962WaterHCID 10476Cyanogen BromideHCID 517045Sodium AcetateHCID 58966440HCID 58966440, compound

Product 1

HCID 58966526HCID 58966526, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the product of step B (873 g, 1.82 mol) in ethanol (4.6 L) was added sodium acetate (452 g, 5.46 mol). The resulting mixture was stirred for 20 minutes and then cyanogen bromide (386 g, 3.64 mol) was added. This mixture was stirred for 2 hours at which point the reaction was complete as evidenced by LC analysis. Water (4 L) was added and volatiles were removed in vacuo. Toluene (4 L) was added and the mixture was stirred until 2 clear layers formed, The layers were separated and the aqueous layer was washed with toluene (2 L). The combined organics were washed with brine (1 L), dried over sodium sulfate, filtered, and concentrated (910 g yield). 1H-NMR (CDCl3) 7.83 (s, 1H), 7.71 (m, 3H), 7.54 (d, 1.7 Hz, 1H), 7.46 (dd, 2.1 Hz, 8.3 Hz, 1H), 4.38 (s, 2H), 4.34 (s, 2H). Mass Spec (ESI): M+1=505.0

Workup

  1. stirringThis mixture was stirred for 2 hours at which
  2. customvolatiles were removed in vacuo
  3. additionToluene (4 L) was added
  4. stirringthe mixture was stirred until 2 clear layers
  5. customformed
  6. customThe layers were separated
  7. washthe aqueous layer was washed with toluene (2 L)
  8. washThe combined organics were washed with brine (1 L)
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. custom(910 g yield)

Sources & evidence

ORD record
ord-f7d41a578ec3488ba7a42518b65e73f4
Source dataset
uspto-grants-2013_02
Patent number
US08383660B2

Reaction notes

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