Hydrochloric Acid → HCID 64157865, compound

HRID 1526528Notes

Reaction equation

HRID 1526528 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:12])=[C:6]([CH:11]=1)/[C:7](/Cl)=[N:8]/[OH:9].[CH2:13]([Cl:16])[CH:14]=[CH2:15].Cl.O>CCOCC.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:12])=[C:6]([C:7]2[CH2:15][CH:14]([CH2:13][Cl:16])[O:9][N:8]=2)[CH:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 7850Allyl chlorideHCID 90389308HCID 90389308, compound

Product 1

HCID 64157865HCID 64157865, compoundYield 52.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

TEA (0.551 ml, 3.96 mmol, Aldrich) was added drop wise to a stirred solution of (Z)-5-bromo-2-fluoro-N-hydroxybenzimidoyl chloride (1c, 1 g, 3.96 mmol) at 0° C., followed by a solution of allyl chloride (0.968 ml, 11.88 mmol, Aldrich) in Et2O (20 mL). The reaction mixture was allowed to stir at RT for 4 hs. 2 M HCl (10 mL) was added, followed by water and EtOAc. The organic phase was separated and dried over MgSO4. The solvent was removed under reduced pressure. The crude material was absorbed onto a plug of silica gel and purified by chromatography eluting with a gradient of 3% to 35% EtOAc in hexane, to provide the title compound as colorless oil (0.604 g, 2.065 mmol, 52.1% yield). MS m/z=293.9 [M+H]+. Calculated for C10H8BrClFNO 292.53.

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over MgSO4
  3. customThe solvent was removed under reduced pressure
  4. customThe crude material was absorbed onto a plug of silica gel
  5. custompurified by chromatography
  6. washeluting with a gradient of 3% to 35% EtOAc in hexane

Sources & evidence

ORD record
ord-423916b13deb4e81af7292102c480a2b
Source dataset
uspto-grants-2015_07
Patent number
US09085576B2

Reaction notes

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