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

HRID 577274Notes

Reaction equation

HRID 577274 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-5e1b829888cb42a3be37cfd3f8ef5800
Source dataset
uspto-grants-2015_05
Patent number
US09040545B2

Reaction notes

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