Ammonium Chloride → HCID 57475762, compound

HRID 1754853Notes

Reaction equation

HRID 1754853 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4](I)[CH:3]=1.C([Mg]Cl)(C)C.[CH2:15]([O:18][CH2:19][C:20](N(OC)C)=[O:21])[CH:16]=[CH2:17].[NH4+].[Cl-]>C1COCC1.O>[CH2:15]([O:18][CH2:19][C:20]([C:4]1[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][C:5]=1[F:8])=[O:21])[CH:16]=[CH2:17]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 27827504-Bromo-1-fluoro-2-iodobenzeneHCID 574757612-(Allyloxy)-N-methoxy-N-methylacetamideHCID 178418918HCID 178418918, compound

Product 1

HCID 57475762HCID 57475762, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Scheme 1, steps C and D: To 4-bromo-1-fluoro-2-iodobenzene (0.95 equiv.) in THF (4.6 mL/g) at 0° C. is added isopropylmagnesium chloride (1.0 equiv, 20 weight percent in THF). After about 60 minutes at 0° C., a solution of 2-(allyloxy)-N-methoxy-N-methylacetamide (1.0 equiv.) (Volumes for this stage are in mL/g of this compound) in THF (2.2 mL/g) is added over about 60 minutes. The reaction mixture is quenched into a solution of NH4Cl (4.3 equiv.) in water (5.8 mL/g) at 0° C. Heptanes (7.2 mL/g) is added as the mixture is warmed to room temperature, and the layers are separated. The organic layer is washed with water (7.2 mL/g). The organic layer is concentrated while additional heptanes (4 mL/g) is added to remove water and THF. The intermediate, 2-allyloxy-1-(5-bromo-2-fluoro-phenyl)ethanone is obtained as a solution in heptanes (approximately 20-25 weight %).

Workup

  1. additionis added over about 60 minutes
  2. customthe layers are separated
  3. washThe organic layer is washed with water (7.2 mL/g)
  4. concentrationThe organic layer is concentrated while additional heptanes (4 mL/g)
  5. additionis added
  6. customto remove water and THF

Sources & evidence

ORD record
ord-afd49852250f4cdc9f4d70d26f84e543
Source dataset
uspto-grants-2015_10
Patent number
US09169271B2

Reaction notes

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