Water → HCID 23299707, compound

HRID 1952775Notes

Reaction equation

HRID 1952775 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1.[CH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[N:16][N:15]=1.O>CCCCCC.O1CCCC1>[F:13][C:10]1[CH:11]=[CH:12][C:7]([CH:17]2[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:14]=[N:15][NH:16]2)=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 962WaterHCID 9207PhthalazineHCID 99931-Bromo-4-fluorobenzeneHCID 178418339Butyllithium

Product 1

HCID 23299707HCID 23299707, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

5.53 ml of a 1.6 M solution of butyllithium in hexane are added dropwise at -78° C. within 20 min. to a solution of 1.48 g of 1-bromo-4-fluoro-benzene in 5 ml of tetrahydrofuran. The resulting white suspension is stirred for a further hour. A solution of 1 g of phthalazine in 5 ml of tetrahydrofuran is added dropwise at -78° C. within 10 min. The reaction mixture is left to warm to room temperature, treated with 50 ml of water and extracted 3 times with 50 ml of dichloromethane each time. The organic phases are combined washed with 50 ml of water and 50 ml of a saturated sodium chloride solution, dried over magnesium sulphate, filtered, the filtrate is concentrated and the residue is chromatographed on 100 g of silica gel with the eluent hexane/ethyl acetate 1:1. 1.49 g (86%) of (RS)-1-(4-fluoro-phenyl)-1,2-dihydro-phthalazine are obtained as a yellow oil. MS: 227 (M+H)+.

Workup

  1. waitThe reaction mixture is left
  2. extractionextracted 3 times with 50 ml of dichloromethane each time
  3. washThe organic phases are combined washed with 50 ml of water and 50 ml of a saturated sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated
  7. customthe residue is chromatographed on 100 g of silica gel with the eluent hexane/ethyl acetate 1:1

Sources & evidence

ORD record
ord-cbe996d3462543f692560c1e4f08d76f
Source dataset
uspto-grants-2000_09
Patent number
US06114330

Reaction notes

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