Carbon tetrabromide → HCID 15099566, compound

HRID 2293858Notes

Reaction equation

HRID 2293858 reaction equation
[C:1]([Br:5])(Br)(Br)[Br:2].[F:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:18]([CH:19]=O)=[C:17]([CH:21]([CH3:23])[CH3:22])[CH:16]=[C:15]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:14]=2)=[CH:9][CH:8]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCl.C(Cl)Cl>[Br:2][C:1]([Br:5])=[CH:19][C:18]1[C:13]([C:10]2[CH:9]=[CH:8][C:7]([F:6])=[CH:12][CH:11]=2)=[N:14][C:15]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:16][C:17]=1[CH:21]([CH3:23])[CH3:22]

Participants

6

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 21471506HCID 21471506, compound

Product 1

HCID 15099566HCID 15099566, compoundYield 98,681%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24526ChlorineSolvent

Procedure

A solution of carbon tetrabromide (2.866 gm, 8.64 mmol) in CH2 Cl2 (8 ml) was added over a 10 minute period to a cold (-10° C.) solution of 2-(4-Fluorophenyl)-4-(1-methylethyl)-6-phenyl-3-pyridinecarboxaldehyde (1.840 gm, 5.76 mmol) (the preparation of which is described in Example 3) and triphenylphosphine (4.590 gm, 17.5 mmol) in CH2Cl2 (30 ml). After the addition was complete, the cooling bath was removed and the mixture was stirred for 20 minutes. The solution was quenched with saturated NaHCO3 and extracted 2× with CH2Cl2. The combined organic layers were washed with saturated NaHCO3, dried (Na2SO4), filtered and concentrated. The concentrate was chromatographed (flash, Merck, SiO2, 1:1 CH2Cl2 : hexane) to give 3-(2,2-Dibromoethenyl)-2-(4-fluorophenyl)-4-(1-methylethyl)-6-phenylpyridine as a white solid (2,701 gm, 99%).

Workup

  1. customthe preparation of which
  2. additionAfter the addition
  3. customthe cooling bath was removed
  4. customThe solution was quenched with saturated NaHCO3
  5. extractionextracted 2× with CH2Cl2
  6. washThe combined organic layers were washed with saturated NaHCO3
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe concentrate was chromatographed (flash, Merck, SiO2, 1:1 CH2Cl2 : hexane)

Sources & evidence

ORD record
ord-82b22fe37ec740fb909f8e2a47a498ca
Source dataset
uspto-grants-1997_11
Patent number
US05686433

Reaction notes

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