Carbon tetrabromide → HCID 14621980, compound

HRID 1720709Notes

Reaction equation

HRID 1720709 reaction equation
[C:1]([Br:5])(Br)(Br)[Br:2].[F:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:16]=[C:15]([CH:25]([CH3:27])[CH3:26])[C:14]=2[CH:28]=O)=[CH:9][CH:8]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:2][C:1]([Br:5])=[CH:28][C:14]1[C:15]([CH:25]([CH3:27])[CH3:26])=[N:16][C:17]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:18][C:13]=1[C:10]1[CH:9]=[CH:8][C:7]([F:6])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 14621979HCID 14621979, compound

Product 1

HCID 14621980HCID 14621980, compoundYield 102.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of carbon tetrabromide (2.204 gm, 6.65 mmol) in CH2Cl2 (8 ml) was added over a 12 minute period to a cold (-12° C.) solution of 4-(4-fluorophenyl)-2-(1-methylethyl)-6-phenyl-3-pyridinecarboxaldehyde (1.415 gm, 4.43 mmol) (the preparation of which is described in Example 1) and triphenylphosphine (3.488 gm, 13.3 mmol) in CH2Cl2 (25 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 3× with CH2Cl2. The combined organic layers were washed with saturated NaHCO3, dried (Na2SO4), filtered and stripped to give a yellow oil. The oil was chromatographed (flash, Merck SiO2, 40% CH2Cl2 in hexane) to give 3-(2,2-dibromoethenyl)-4-(4-fluorophenyl)-2-(1-methylethyl)-6-phenylpyridine as a colorless foam (2.152 gm, 100%).

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 3× with CH2Cl2
  6. washThe combined organic layers were washed with saturated NaHCO3
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customto give a yellow oil
  10. customThe oil was chromatographed (flash, Merck SiO2, 40% CH2Cl2 in hexane)

Sources & evidence

ORD record
ord-40bd2d37f03a464bb21fb06ecc79d9c0
Source dataset
uspto-grants-1996_04
Patent number
US05506219

Reaction notes

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