Hydrochloric Acid → 3-Bromo-4-fluorobenzyl Alcohol

HRID 851633Notes

Reaction equation

HRID 851633 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Br:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[F:15])[C:9](O)=[O:10].[BH4-].[Na+].Cl>COCCOCCOC.COC(C)(C)C.O>[F:15][C:14]1[CH:13]=[CH:12][C:8]([CH2:9][OH:10])=[CH:7][C:6]=1[Br:5]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 705093-Bromo-4-fluorobenzoic acidHCID 4311764Sodium borohydrideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 27733513-Bromo-4-fluorobenzyl AlcoholYield 76%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8150DiglymeSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
20 °C

Procedure

6.7 g of aluminum chloride were added to a solution of 10.9 g of 95% pure 3-bromo-4-fluorobenzoic acid in 150 ml of diglyme at 20° C. The reaction mixture was subsequently stirred at 20° C. for 10 minutes and 5.7 g of sodium borohydride were then added in portions at 20° to 25° C. After 12 hours, about 100 ml of water (vigorous foaming) and then about 1 ml of 10% strength hydrochloric acid were added dropwise. About 100 ml of tert.-butyl methyl ether were added and the organic phase was separated off. It was washed once with about 30 ml of saturated sodium bicarbonate solution. The ether phase was then concentrated. 6.7 g (76% of theory) of 4-fluoro-3-bromo-benzyl alcohol were obtained.

Workup

  1. waitAfter 12 hours
  2. customthe organic phase was separated off
  3. washIt was washed once with about 30 ml of saturated sodium bicarbonate solution
  4. concentrationThe ether phase was then concentrated

Sources & evidence

ORD record
ord-3b3d4e5013d84e15b53eef3f7290b64f
Source dataset
uspto-grants-1983_05
Patent number
US04386035

Reaction notes

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