Water → HCID 22220046, compound

HRID 732999Notes

Reaction equation

HRID 732999 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([I:10])=[CH:6][C:3]=1[CH:4]=[O:5].[BH4-].[Na+].O>C(O)(C)C>[F:1][C:2]1[CH:9]=[CH:8][C:7]([I:10])=[CH:6][C:3]=1[CH2:4][OH:5]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 162170582-Fluoro-5-iodobenzaldehyde

Product 1

HCID 22220046HCID 22220046, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 2-fluoro-5-iodobenzaldehyde (1.173 g, 4.692 mmol) in isopropanol (25 mL) was treated with sodium borohydride (0.379 g, 10.02 mmol), stirred at room temperature for 18 h, poured into water (125 mL), and extracted with isopropyl ether (2×25 mL). The combined organic phase was dried (Na2SO4), and concentrated in vacuo to give the title compound (1.187 g, 99%) as a pale yellow solid; NMR δH (400 MHz, CDCl3) 7.77 (1H, m), 7.57 (1H, m), 6.82 (1H, t, J 8.8 Hz), 4.73 (2H, d, J 6.1 Hz), and 1.79 (1H, t, J 6.1 Hz).

Workup

  1. extractionextracted with isopropyl ether (2×25 mL)
  2. dry with materialThe combined organic phase was dried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9fc120ee43354e69bf2645a2f75ee58b
Source dataset
uspto-grants-2009_09
Patent number
US07589097B2

Reaction notes

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