Water → 3-Bromo-4-fluorobenzyl Alcohol

HRID 414500Notes

Reaction equation

HRID 414500 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[F:16])[CH:11]=[O:12].O>O1CCCC1>[Br:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[F:16])[CH2:11][OH:12]

Participants

5

Reactant 3

HCID 962WaterHCID 1736043-Bromo-4-fluorobenzaldehydeHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 27733513-Bromo-4-fluorobenzyl Alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (0.075 g) was added to a stirred solution of 3-bromo-4-fluorobenzaldehyde (1.2 g) in dry tetrahydrofuran (20 cm3), the temperature being maintained below 5° C. by external cooling. The temperature of the reaction mixture was then allowed to rise to the ambient value (ca 20° C.) and the mixture was stirred for 2 hours; GLC analysis of a withdrawn sample indicated 82% conversion at this time, and further lithium aluminium hydride (0.025 g) was therefore added to the mixture. After a further 1.5 hours GLC analysis indicated that the reaction was complete. The mixture aas poured into water (20 cm3) and the products extracted into diethyl ether (3×20 cm3). The combined ethereal extracts were washed with brine and dried over anhydrous magnesium sulphate. Evaporation of the solvent under reduced pressure gave the title compound in high purity.

Workup

  1. temperaturethe temperature being maintained below 5° C. by external cooling
  2. customto rise to the ambient value (ca 20° C.)
  3. additionwas therefore added to the mixture
  4. waitAfter a further 1.5 hours GLC analysis indicated that the reaction
  5. extractionthe products extracted into diethyl ether (3×20 cm3)
  6. washThe combined ethereal extracts were washed with brine
  7. dry with materialdried over anhydrous magnesium sulphate
  8. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-ee7cf75197364c4ea814938ba3805bf5
Source dataset
uspto-grants-1988_12
Patent number
US04792563

Reaction notes

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