Sodium borohydride → HCID 67516027, compound

HRID 2173274Notes

Reaction equation

HRID 2173274 reaction equation
[F:1][C:2]1[C:3]([I:13])=[C:4]([CH2:8][C:9](OC)=[O:10])[CH:5]=[CH:6][CH:7]=1.[Cl-].[Cl-].[Ca+2].[BH4-].[Na+]>C(O)C>[F:1][C:2]1[C:3]([I:13])=[C:4]([CH2:8][CH2:9][OH:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 86693010HCID 86693010, compound

Product 1

HCID 67516027HCID 67516027, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl (3-fluoro-2-iodophenyl)acetate (1.2 g, 4 mmol) in 25 mL of ethanol was cooled to 0˜5° C., CaCl2 (900 mg, 8 mmol) was added and the mixture was stirred at 0˜5° C. for 10 min. NaBH4(600 mg, 15.7 mmol) was added slowly. The reaction was warmed to room temperature and stirred at room temperature for 2 hours. Recooled to 0˜5° C., quenched with aqueous citric acid solution, extracted with EtOAc. The organic layers were washed with water and brine, dried over anhydrous sodium sulfate and concentrated to get 2-(3-fluoro-2-iodophenyl)ethanol. 1H-NMR (400 MHz, CDCl3) δ ppm 7.15˜7.20 (m, 1H), 6.99˜7.00 (m, 1H), 6.84˜6.88 (m, 1H), 3.81 (t, J=7.0 Hz, 2H), 3.02 (t, J=7.0 Hz, 2H).

Workup

  1. stirringstirred at room temperature for 2 hours
  2. customRecooled to 0˜5° C.
  3. customquenched with aqueous citric acid solution
  4. extractionextracted with EtOAc
  5. washThe organic layers were washed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5635ed2464cf4041967d1544ef66edfd
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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