Carbon tetrabromide → HCID 21471314, compound

HRID 2295212Notes

Reaction equation

HRID 2295212 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>ClCl>[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 24526ChlorineSolvent2×

Procedure

A solution of carbon tetrabromide (12.620 gm, 38.0 mmol) in CH2 Cl2 (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 CH2 Cl2 (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-b9346783117148f3b29ed8117af2484f
Source dataset
uspto-grants-1997_11
Patent number
US05691322

Reaction notes

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