Hydrogen Bromide → (4-Bromo-3-trifluoromethyl-phenyl)-morpholin-4-yl-methanone

HRID 2199733Notes

Reaction equation

HRID 2199733 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[O:9])=[CH:4][C:3]=1[C:16]([F:19])([F:18])[F:17].OS(O)(=O)=O.N([O-])=O.[Na+].[BrH:29]>O>[Br:29][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[O:9])=[CH:4][C:3]=1[C:16]([F:19])([F:18])[F:17]

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 1118Sulfuric AcidHCID 23668193Sodium NitriteHCID 62155530(4-Amino-3-(trifluoromethyl)phenyl)(morpholino)methanone

Product 1

HCID 68941524(4-Bromo-3-trifluoromethyl-phenyl)-morpholin-4-yl-methanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixture of EXAMPLE 144B (8.3 g) was added water (75 mL) and H2SO4 (25 mL). The mixture was stirred at 0° C. while NaNO2 (3.13 g) in water (30 mL) was added. After stirring for 1 hour, the mixture was added to CuBr (5.45 g) in 48% HBr (200 mL). This mixture was stirred at 60° C. for 3 hours, cooled to room temperature, and partitioned between water and ethyl acetate. The organic layer was washed with aqueous Na2CO3 and dried (Na2SO4), filtered and concentrated.

Workup

  1. additionwas added
  2. stirringThis mixture was stirred at 60° C. for 3 hours
  3. custompartitioned between water and ethyl acetate
  4. washThe organic layer was washed with aqueous Na2CO3
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b85f67f6aad84585abbb676ab5d92dee
Source dataset
uspto-grants-2016_06
Patent number
US09359296B2

Reaction notes

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