HCID 89443501, compound → HCID 89445228, compound

HRID 1771708Notes

Reaction equation

HRID 1771708 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:20])=[C:6]([CH:19]=1)[C:7]([NH:9][C:10]1[C:15]([F:16])=[CH:14][CH:13]=[C:12]([OH:17])[C:11]=1[F:18])=O>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:20])=[C:6]([CH2:7][NH:9][C:10]2[C:11]([F:18])=[C:12]([OH:17])[CH:13]=[CH:14][C:15]=2[F:16])[CH:19]=1

Participants

3

Reactant 1

HCID 89443501HCID 89443501, compound

Product 1

HCID 89445228HCID 89445228, compoundYield 223.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 5-bromo-N-(2,6-difluoro-3-hydroxy-phenyl)-2-fluoro-benzamide (5.78 g, 7.1 mmol, 1.0 eq) in THF (100 mL) at 0° C. under N2 was added a solution of BH3 (1M in THF, 83.5 mL, 83.5 mmol, 5.0 eq) dropwise. The reaction mixture was heated at 60° C. overnight then cooled to room temperature and quenched with water. The aqueous layer was extracted with EtOAc and the combined organic extracts were washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by column chromatography (petroleum ether:EtOAc, 30:1 to 20:1) to give the title compound as a brown oil (5.26 g, 94%).

Workup

  1. temperaturethen cooled to room temperature
  2. customquenched with water
  3. extractionThe aqueous layer was extracted with EtOAc
  4. washthe combined organic extracts were washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue was purified by column chromatography (petroleum ether:EtOAc, 30:1 to 20:1)

Sources & evidence

ORD record
ord-ccafb6c1cf1f4ef587e823723b3230dd
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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