Methyl chloroformate → 3-Bromo-4-fluorobenzyl Alcohol

HRID 851636Notes

Reaction equation

HRID 851636 reaction equation
C(N(CC)CC)C.[Br:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[F:18])[C:12](O)=[O:13].COC(Cl)=O>O1CCCC1>[Br:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[F:18])[CH2:12][OH:13]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 705093-Bromo-4-fluorobenzoic acid

Product 1

HCID 27733513-Bromo-4-fluorobenzyl AlcoholYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2 g of triethylamine, dissolved in 5 ml of tetrahydrofuran, were added dropwise to a solution of 4.2 g of 3-bromo-4-fluoro-benzoic acid and 1.95 g of chloroformic acid methyl ester in 30 ml of tetrahydrofuran at 20° C., while stirring. Stirring was continued for a further 40 minutes at 20°-25° C. and the hydrochloride which had precipitated was then filtered off. 5.5 g of sodium borohydride, dissolved in 20 ml of water, were added dropwise to the filtrate at 10° to 20° C., while stirring. Stirring was then continued for a further 4 hours at 20° C. The reaction batch was subsequently poured into 100 ml of water and extracted by shaking with 80 ml of methylene chloride. The methylene chloride phase was separated off and dried over magnesium sulphate and the solvent was then distilled off in vacuo. 1.95 g (95% of theory) of 3-bromo-4-fluoro-benzyl alcohol were obtained as a colorless oil.

Workup

  1. stirringStirring
  2. customthe hydrochloride which had precipitated
  3. filtrationwas then filtered off
  4. dissolution5.5 g of sodium borohydride, dissolved in 20 ml of water
  5. additionwere added dropwise to the filtrate at 10° to 20° C.
  6. stirringwhile stirring
  7. stirringStirring
  8. waitwas then continued for a further 4 hours at 20° C
  9. additionThe reaction batch was subsequently poured into 100 ml of water
  10. extractionextracted
  11. stirringby shaking with 80 ml of methylene chloride
  12. customThe methylene chloride phase was separated off
  13. dry with materialdried over magnesium sulphate
  14. distillationthe solvent was then distilled off in vacuo

Sources & evidence

ORD record
ord-ac9c416c3bb14ad086699599b2d18a4b
Source dataset
uspto-grants-1983_05
Patent number
US04386035

Reaction notes

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