Lithium borohydride → (2-Fluoro-3-morpholinophenyl)methanol

HRID 595000Notes

Reaction equation

HRID 595000 reaction equation
[F:1][C:2]1[C:16]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[CH:15][CH:14]=[CH:13][C:3]=1[C:4](OCCOCCBr)=[O:5].[BH4-].[Li+]>C1COCC1>[F:1][C:2]1[C:16]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 667651712-(2-Bromoethoxy)ethyl 2-fluoro-3-morpholinobenzoate

Product 1

HCID 66765145(2-Fluoro-3-morpholinophenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(2-bromoethoxy)ethyl 2-fluoro-3-morpholinobenzoate (450 mg, 1.2 mmol) in THF (5 mL) was added lithium borohydride (1.5 eq) and the reaction stirred at rt for 18 h. The reaction was quenched by addition of saturated NH4Cl (aq) and extracted with EtOAc. The organic phase was dried (Na2SO4), filtered and concentrated in vacuo. The resultant residue was purified by column chromatography (petroleum ether: EtOAc) to give (2-fluoro-3-morpholinophenyl)methanol.

Workup

  1. customThe reaction was quenched by addition of saturated NH4Cl (aq)
  2. extractionextracted with EtOAc
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resultant residue was purified by column chromatography (petroleum ether: EtOAc)

Sources & evidence

ORD record
ord-f87401f5016a497a8fe2101d9a14c525
Source dataset
uspto-grants-2016_01
Patent number
US09242987B2

Reaction notes

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