Sodium borohydride → 1-Bromo-3-fluorobenzyl alcohol

HRID 1670596Notes

Reaction equation

HRID 1670596 reaction equation
[Br:1][C:2]1([CH:9]=[CH:8][CH:7]=[C:6]([F:10])[CH2:5]1)[CH:3]=[O:4].[BH4-].[Na+]>CO.C(OCC)(=O)C>[Br:1][C:2]1([CH:9]=[CH:8][CH:7]=[C:6]([F:10])[CH2:5]1)[CH2:3][OH:4]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 866319341-Bromo-3-fluorobenzaldehyde

Product 1

HCID 673357701-Bromo-3-fluorobenzyl alcoholYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 1-bromo-3-fluorobenzaldehyde (1.60 kg, 7.91 mol) in methanol (14 L) at 0° C. add sodium borohydride (284 g, 7.93 mol) in portions over 30 min to control the exotherm and gas evolution. After 15 min, quench with water (500 mL) and concentrate to obtain a yellow oil. Dissolve the oil in ethyl acetate (6 L) and wash with water (3 L). Extract the aqueous layer with ethyl acetate (1 L). Wash the combined organic phases with brine (2 L), dry over sodium sulfate, filter, and concentrate to obtain the title compound as an orange oil (1614 g, 100%). 1H NMR (CDCl3) δ 7.40 (d, 1H), 7.18 (m, 1H), 7.07 (t, 1H), 4.86 (s, 2H).

Workup

  1. customquench with water (500 mL)
  2. concentrationconcentrate
  3. customto obtain a yellow oil
  4. washwash with water (3 L)
  5. extractionExtract the aqueous layer with ethyl acetate (1 L)
  6. washWash the combined organic phases with brine (2 L)
  7. dry with materialdry over sodium sulfate
  8. filtrationfilter
  9. concentrationconcentrate

Sources & evidence

ORD record
ord-5d0c13cdd0a249bb8b46752edce60c5b
Source dataset
uspto-grants-2011_08
Patent number
US07994164B2

Reaction notes

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