1-Bromo-3-chloropropane → HCID 19418907, compound

HRID 864359Notes

Reaction equation

HRID 864359 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][N:5]1[C:10](=[O:11])[C:9]2[CH:12]=[CH:13][C:14](F)=[CH:15][C:8]=2[Si:7]([CH3:18])([CH3:17])[CH2:6]1.C[Si]1(C)C2C=CC=C([F:30])C=2C(=O)NC1.C([Li])CCC.ClCCCBr>O1CCCC1>[Cl:1][CH2:2][CH2:3][CH2:4][N:5]1[C:10](=[O:11])[C:9]2[C:12]([F:30])=[CH:13][CH:14]=[CH:15][C:8]=2[Si:7]([CH3:18])([CH3:17])[CH2:6]1

Participants

6

Reactant 4

HCID 80061-Bromo-3-chloropropaneHCID 19418908HCID 19418908, compoundHCID 19418913HCID 19418913, compoundHCID 178418339Butyllithium

Product 1

HCID 19418907HCID 19418907, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(3-Chloropropyl)-1,1-dimethyl-5-fluoro-4-oxo-1,2,3,4-tetrahydro-3,1-benzazasiline is obtained in a manner similar to that described in Example 11 for the preparation of 3-(3-chloropropyl)-1,1-dimethyl-7-fluoro-4-oxo-1,2,3,4-tetrahydro-3,1-benzazasiline, but using 3.15 g of 1,1-dimethyl-5-fluoro-4-oxo-1,2,3,4-tetrahydro-3,1-benzazasiline, 11.3 cm3 of n-butyllithium, 5.7 g of 1-chloro-3-bromopropane and 65 cm3 of tetrahydrofuran. After purification by flash chromatography on a silica column under a nitrogen stream at moderate pressure (0.5-1.5 bar) with a dichloromethane-methanol mixture (99.5-0.5 by volume) as eluent, 1.15 g of 3-(3-chloropropyl)-1,1-dimethyl-5-fluoro-4-oxo 1,2,3,4-tetrahydro-3,1-benzazasiline are obtained.

Workup

  1. customAfter purification by flash chromatography on a silica column under a nitrogen stream at moderate pressure (0.5-1.5 bar) with a dichloromethane-methanol mixture (99.5-0.5 by volume) as eluent

Sources & evidence

ORD record
ord-4f2c50128b1945d4b8ba866724286311
Source dataset
uspto-grants-1996_10
Patent number
US05563144

Reaction notes

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