Sodium borohydride → (5-Fluoro-2-hydroxymethyl-4-iodo-phenyl)-methanol

HRID 1930949Notes

Reaction equation

HRID 1930949 reaction equation
C[O:2][C:3](=O)[C:4]1[C:5](=[CH:10][C:11]([F:15])=[C:12]([I:14])[CH:13]=1)[C:6](OC)=[O:7].[Cl-].[Ca+2].[Cl-].[BH4-].[Na+]>C(O)C>[F:15][C:11]1[C:12]([I:14])=[CH:13][C:4]([CH2:3][OH:2])=[C:5]([CH2:6][OH:7])[CH:10]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 577534144-Fluoro-5-iodo-phthalic acid dimethyl ester

Product 1

HCID 57753608(5-Fluoro-2-hydroxymethyl-4-iodo-phenyl)-methanolYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 9.38 mmol 4-fluoro-5-iodo-phthalic acid dimethyl ester in 25 ml absolute ethanol was added 9.38 mmol calcium chloride. 18.8 mmol sodium borohydride was then added in small portions and the reaction mixture was stirred for 4 h at room temperature, then at reflux for 2 h and then at room temperature overnight. The mixture was quenched by addition of 20 ml 1 M aq. hydrochloric acid and diluted with water and ethyl acetate. The phases were separated and the organic phase was extracted four times with dichloromethane. The combined organic extracts were dried over sodium sulfate and concentrated in vacuo to afford the title compound as a yellow oil (98% yield). MS (m/e): 283.1 ([M+H]+, 100%).

Workup

  1. temperatureat reflux for 2 h
  2. customat room temperature
  3. customovernight
  4. customThe mixture was quenched by addition of 20 ml 1 M aq. hydrochloric acid
  5. additiondiluted with water and ethyl acetate
  6. customThe phases were separated
  7. extractionthe organic phase was extracted four times with dichloromethane
  8. dry with materialThe combined organic extracts were dried over sodium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e6b01af3e409474e9545ec99822717a5
Source dataset
uspto-grants-2012_05
Patent number
US08188139B2

Reaction notes

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