Water → HCID 84766583, compound

HRID 1772871Notes

Reaction equation

HRID 1772871 reaction equation
[Li+].[BH4-].[F:3][C:4]1[CH:13]=[C:12]([F:14])[CH:11]=[C:10]([O:15][CH3:16])[C:5]=1[C:6](OC)=[O:7].O>C1COCC1>[F:3][C:4]1[CH:13]=[C:12]([F:14])[CH:11]=[C:10]([O:15][CH3:16])[C:5]=1[CH2:6][OH:7]

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 90022261HCID 90022261, compound

Product 1

HCID 84766583HCID 84766583, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of LiBH4 (2M in THF, 6.28 mL, 12.6 mmol) was added to a solution of methyl 2,4-difluoro-6-methoxybenzoate (1.15 g, 5.71 mmol) in THF (30 mL). The solution was stirred at rt for 23 h, then at 60° C. for 4.5 h, and reflux for 18.5 h. After cooling to rt, H2O (20 mL) was added dropwise and the mixture stirred for 5 min before being partially concentrated in vacuo. DCM (20 mL) was added, the phases were separated, and the aqueous phase was extracted with DCM (2×10 mL). The organic layers were concentrated in vacuo to yield the title compound (978 mg, 5.62 mmol).

Workup

  1. waitat 60° C. for 4.5 h
  2. temperaturereflux for 18.5 h
  3. temperatureAfter cooling to rt
  4. stirringthe mixture stirred for 5 min
  5. concentrationbefore being partially concentrated in vacuo
  6. additionDCM (20 mL) was added
  7. customthe phases were separated
  8. extractionthe aqueous phase was extracted with DCM (2×10 mL)
  9. concentrationThe organic layers were concentrated in vacuo

Sources & evidence

ORD record
ord-27396ec92ac1413fb8c59b05b10273a0
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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