Water → (4-Bromo-2,3,5,6-tetrafluorophenyl)methanol

HRID 654613Notes

Reaction equation

HRID 654613 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[C:11]([F:12])=[C:10]([F:13])[C:7]([CH:8]=[O:9])=[C:6]([F:14])[C:5]=1[F:15].O>CO>[Br:3][C:4]1[C:5]([F:15])=[C:6]([F:14])[C:7]([CH2:8][OH:9])=[C:10]([F:13])[C:11]=1[F:12]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 136705704-Bromo-2,3,5,6-tetrafluorobenzaldehyde

Product 1

HCID 13670571(4-Bromo-2,3,5,6-tetrafluorophenyl)methanolYield 90.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-5 °C

Procedure

Sodium borohydride (1.0 g) was added portionwise over a period of 30 minutes to a stirred solution of 4-bromo-2,3,5,6-tetrafluorobenzaldehyde (8.2 g) in methanol (80 cm3) whilst the temperature was maintained within the range from -5° C. to ±5° C., after which the mixture was stirred for 2 hours at the ambient temperature (ca 18° C.). The mixture was poured into water and the precipitated white solid collected by filtration, washed with water and air dried to yield 4-bromo-2,3,5,6-tetrafluorobenzyl alcohol (7.5 g), mp. 60°-62° C.

Workup

  1. customto ±5° C.
  2. filtrationthe precipitated white solid collected by filtration
  3. washwashed with water and air
  4. customdried

Sources & evidence

ORD record
ord-72f2809f15c547fc9320e8bf665dcfb7
Source dataset
uspto-grants-1992_07
Patent number
US05132469

Reaction notes

Loading…