Hydrochloric Acid → (3,5-Dibromo-4-methylphenyl)methanol

HRID 1803593Notes

Reaction equation

HRID 1803593 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Br:13])[C:11]=1[CH3:12])[C:5](OC)=[O:6].[BH4-].[Na+].Cl>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:9]=[C:10]([Br:13])[C:11]=1[CH3:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 624016Methyl 3,5-dibromo-4-methylbenzoateHCID 4311764Sodium borohydride

Product 1

HCID 60156325(3,5-Dibromo-4-methylphenyl)methanolYield 72.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of methyl 3,5-dibromo-4-methylbenzoate (15 g, 48.706 mmol), NaBH4 (5.53 g, 146.18 mmol) and absolute ethanol (175 mL) was heated to reflux for 4 h. The mixture was cooled, followed by acidification with 2N HCl. The solids were filtered through celite and rinsed with EtOAc. The filtrate was poured onto water and extracted. The organic layer was washed with brine and dried (Na2SO4). Chromatography (Hexanes/EtOAc) afforded (3,5-dibromo-4-methyl-phenyl)-methanol (9.94 g) as a white solid. 1H NMR (400 MHz, d6-DMSO) δ: 2.48 (s, 3H), 4.45 (d, 2H), 5.38 (t, 1H), 7.57 (s, 2H) ppm.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 h
  3. temperatureThe mixture was cooled
  4. filtrationThe solids were filtered through celite
  5. washrinsed with EtOAc
  6. additionThe filtrate was poured onto water
  7. extractionextracted
  8. washThe organic layer was washed with brine
  9. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-32c6f6564733463eb0c4f9ebc6c1b20c
Source dataset
uspto-grants-2013_01
Patent number
US08349836B2

Reaction notes

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