Carbon tetrabromide → HCID 21471314, compound

HRID 1720721Notes

Reaction equation

HRID 1720721 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:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=[C:15]([CH:23]([CH3:25])[CH3:24])[C:14]=2[CH:26]=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:26][C:14]1[C:15]([CH:23]([CH3:25])[CH3:24])=[N:16][C:17]2[C:22]([C:13]=1[C:10]1[CH:11]=[CH:12][C:7]([F:6])=[CH:8][CH:9]=1)=[CH:21][CH:20]=[CH:19][CH:18]=2

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 14780564HCID 14780564, compound

Product 1

HCID 21471314HCID 21471314, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of carbon tetrabromide (12.620 gm, 38.0 mmol) in CH2Cl2 (20 ml) was added over a 10 minute period to a cold (-10° C.) solution of 4-(4-Fluorophenyl)-2-(1-methylethyl)-3-quinolinecarboxaldehyde (7.394 gm, 25.2 mmol) and triphenylphosphine (19.86 gm, 75.7 mmol) in CH2Cl2 (140 ml). After the addition was complete, the mixture was stirred for 20 minutes then quenched with saturated NaHCO3 and extracted 2× with CH2Cl2. The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated to 50 ml. The residue was triturated with Et2O and the precipitated triphenylphosphine oxide was removed by filtration. The filtrate was stripped and the residue was chromatographed (flash, Merck SiO2, 10% EtOAc in hexane) to give 3-(2,2-Dibromoethenyl)-4-(4-fluorophenyl)-2-(1 -methylethyl)quinoline as a light yellow foamy oil (11.556 gm, 102% theory).

Workup

  1. additionAfter the addition
  2. customthen quenched with saturated NaHCO3
  3. extractionextracted 2× with CH2Cl2
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated to 50 ml
  8. customThe residue was triturated with Et2O
  9. customthe precipitated triphenylphosphine oxide was removed by filtration
  10. customthe residue was chromatographed (flash, Merck SiO2, 10% EtOAc in hexane)

Sources & evidence

ORD record
ord-3a949bc74d3749ed974de45b390ae5a3
Source dataset
uspto-grants-1996_04
Patent number
US05506219

Reaction notes

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