Formaldehyde → 2-(2-Bromo-6-nitrophenyl)ethan-1-ol

HRID 963756Notes

Reaction equation

HRID 963756 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[CH3:11].[CH2:12]=[O:13]>C(O)(C)(C)C.CS(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[CH2:11][CH2:12][OH:13]

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 1235372-Bromo-6-nitrotoluene

Product 1

HCID 190827272-(2-Bromo-6-nitrophenyl)ethan-1-olYield 70%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
70 °C

Procedure

A solution of potassium tertiary-butylate (90 mg, 0.8 mmol) in tert-butanol (1 ml, synthesis quality, 99%) was added to 2-bromo-6-nitrotoluene (1.08 g, 5 mmol) and paraformaldehyde (150 mg, 5 mmol in DMSO (2.5 ml, synthesis quality, additionally dried for 2 d over molecular sieve 4 Å). After the addition of the potassium tertiary-butylate solution, a color change from yellow to deep violet occurred. It was stirred for 5 min at room temperature and for 30 min at 70° C. (oil bath temperature). The mixture was then allowed to cool to room temperature and neutralized with a few drops of conc. HCl. The mixture was diluted with EtOAc (30 ml) and washed with H2O (20 ml). The aqueous phase was post-extracted with EtOAc (2×20 ml). Drying of the organic phases over Na2 SO4, filtering and evaporating the solvent under reduced pressure yielded the crude product (1.49 g) which was purified by column chromatography (20 g SiO2, 20×2 cm, solvent: PE 45 ml, PE/EtAOc 10:1 110 ml, 8:1 180 ml, 7.5:1 340 ml, 6:1 140 ml). 2-(2-bromo-6-nitrophenyl)ethanol (867 mg, 70%) was obtained as a yellow solid.

Workup

  1. custom2.5 ml, synthesis quality
  2. customadditionally dried for 2 d over molecular sieve 4 Å)
  3. additionAfter the addition of the potassium tertiary-butylate solution
  4. temperatureto cool to room temperature and neutralized with a few drops of conc. HCl
  5. additionThe mixture was diluted with EtOAc (30 ml)
  6. washwashed with H2O (20 ml)
  7. extractionThe aqueous phase was post-extracted with EtOAc (2×20 ml)
  8. customDrying of the organic phases over Na2 SO4
  9. filtrationfiltering
  10. customevaporating the solvent under reduced pressure
  11. customyielded the crude product (1.49 g) which
  12. customwas purified by column chromatography (20 g SiO2, 20×2 cm, solvent: PE 45 ml, PE/EtAOc 10:1 110 ml, 8:1 180 ml, 7.5:1 340 ml, 6:1 140 ml)

Sources & evidence

ORD record
ord-32317d21785c41a7a02353ecd597510a
Source dataset
uspto-grants-1998_06
Patent number
US05763599

Reaction notes

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