Hydrogen Bromide → HCID 117676185, compound

HRID 1506884Notes

Reaction equation

HRID 1506884 reaction equation
N[C:2]1[CH:7]=[C:6]([F:8])[C:5]([CH:9]([CH3:14])[C:10]([O:12][CH3:13])=[O:11])=[C:4]([F:15])[CH:3]=1.[BrH:16].N([O-])=O.[Na+].S(=O)(=O)(O)O.Cl>CO>[Br:16][C:2]1[CH:7]=[C:6]([F:8])[C:5]([CH:9]([CH3:14])[C:10]([O:12][CH3:13])=[O:11])=[C:4]([F:15])[CH:3]=1

Participants

7

Reactant 5

HCID 260Hydrogen BromideHCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 23668193Sodium NitriteHCID 117046299HCID 117046299, compound

Product 1

HCID 117676185HCID 117676185, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of compound (29b) (6.7 g, 31.3 mmol) in 40% hydrobromic acid (18.4 mL, 125 mmol) was treated with an aqueous solution (38 mL) of sodium nitrite (2.4 g, 33.8 mmol), CuBr (2.5 g, 17.5 mmol), and 96% sulfuric acid (0.1 mL) in the same manner as in (i) above. The obtained product was further dissolved in methanol (100 mL), and a catalytic amount of concentrated hydrochloric acid (0.2 mL) was added thereto and treated in the same manner. The obtained residue was subjected to silica gel column chromatography and elution with an n-hexane/ethyl acetate (4:1) solution to give 6.1 g (70%) of compound (30b) as pale yellow liquid matter.

Workup

  1. additiontreated in the same manner
  2. washThe obtained residue was subjected to silica gel column chromatography and elution with an n-hexane/ethyl acetate (4:1) solution

Sources & evidence

ORD record
ord-23ee3a2648c149bfa11e913b154cf674
Source dataset
uspto-grants-2015_12
Patent number
US09221786B2

Reaction notes

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