Carbon tetrabromide → HCID 57910796, compound

HRID 1968662Notes

Reaction equation

HRID 1968662 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][C:21]([C:39]1[CH:44]=[CH:43][C:42]([C:45]2[O:49][N:48]=[C:47]([CH2:50]O)[CH:46]=2)=[CH:41][CH:40]=1)([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=2)=[CH:27][N:26]=1)[CH:22]([CH3:24])[CH3:23].C(Br)(Br)(Br)[Br:53].C(=O)(O)[O-].[Na+]>C1COCC1>[Br:53][CH2:50][C:47]1[CH:46]=[C:45]([C:42]2[CH:43]=[CH:44][C:39]([C:21]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=4)=[CH:27][N:26]=3)([CH3:20])[CH:22]([CH3:24])[CH3:23])=[CH:40][CH:41]=2)[O:49][N:48]=1

Participants

6

Reactant 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 57910810HCID 57910810, compound

Product 1

HCID 57910796HCID 57910796, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triphenylphosphine (1.34 g, 5.21 mmol) was added to a stirred solution of 1d (1.49 g, 3.47 mmol) and carbon tetrabromide (1.73 g, 5.21 mmol) in THF (100 mL) at rt. After approximately 1.5 h, the reaction mixture was poured into saturated aqueous sodium bicarbonate and extracted three times with EtOAc. The combined organic extracts were dried (magnesium sulfate), concentrated in vacuo, and the crude residue was purified by flash chromatography on silica gel (gradient elution; 0%-70% EtOAc/hexanes as eluent) to afford the title compound 1e. m/z (ES) 494 (MH)+.

Workup

  1. extractionextracted three times with EtOAc
  2. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  3. concentrationconcentrated in vacuo
  4. customthe crude residue was purified by flash chromatography on silica gel (gradient elution; 0%-70% EtOAc/hexanes as eluent)

Sources & evidence

ORD record
ord-4281f7d55bb44893beab8ad316d133a1
Source dataset
uspto-grants-2013_04
Patent number
US08426413B2

Reaction notes

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