Triphenylphosphane dibromide → 4-Bromo-7-chloroquinoline

HRID 2090050Notes

Reaction equation

HRID 2090050 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](O)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[Br-:13].[Br-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CC#N>[Br:13][C:6]1[C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 12890784Triphenylphosphane dibromideHCID 178516426HCID 178516426, compound

Product 1

HCID 109776384-Bromo-7-chloroquinoline

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 7-chloroquinolin-4-ol (10.0 g, 55.7 mmol) and triphenylphosphine dibromide (35.3 g, 83.6 mmol) in CH3CN (370 mL) was refluxed for 16 hours then cooled to room temperature. The resulting precipitate was collected by vacuum filtration and washed with CH3CN (2×70 mL). The precipitate was then partitioned between CH2Cl2 (300 mL) and 1 M NaOH (aq) (300 mL). The aqueous phase was extracted with CH2Cl2 (100 mL). The combined organics were dried over Na2SO4, filtered, and concentrated to afford the title compound as a white solid: 1H NMR (500 MHz, CDCl3): δ 8.67 (d, J=4.7 Hz, 1H); 8.14 (d, J=9.0 Hz, 1H); 8.11 (d, J=2.1 Hz, 1H); 7.70 (d, J=4.7 Hz, 1H); 7.60 (dd, J=9.0, 2.1 Hz, 1H); LC4 1.86 min. (M+H)=244.

Workup

  1. temperaturewas refluxed for 16 hours
  2. filtrationThe resulting precipitate was collected by vacuum filtration
  3. washwashed with CH3CN (2×70 mL)
  4. customThe precipitate was then partitioned between CH2Cl2 (300 mL) and 1 M NaOH (aq) (300 mL)
  5. extractionThe aqueous phase was extracted with CH2Cl2 (100 mL)
  6. dry with materialThe combined organics were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c19ea9990faa4a4fac6ef1e19b52a394
Source dataset
uspto-grants-2013_05
Patent number
US08436015B2

Reaction notes

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