Triethylamine → 2-Hydroxy-3-bromo-5-(1,1-dimethylethyl)-benzonitrile

HRID 1709999Notes

Reaction equation

HRID 1709999 reaction equation
[OH:1][C:2]1[C:10]([Br:11])=[CH:9][C:8]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:7][C:3]=1[CH:4]=[N:5]O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(N(CC)CC)C>O1CCCC1>[OH:1][C:2]1[C:10]([Br:11])=[CH:9][C:8]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:7][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 1363645842-Hydroxy-3-bromo-5-(1,1-dimethylethyl)benzaldehyde oxime

Product 1

HCID 230354202-Hydroxy-3-bromo-5-(1,1-dimethylethyl)-benzonitrileYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 12.0 g (44.0 mmol) of 2-hydroxy-3-bromo-5-(1,1-dimethylethyl)benzaldehyde oxime and 18.9 g (90.0 mmol) of trifluoroacetic anhydride in 100 ml of tetrahydrofuran was cooled in an ice-water bath. A solution of 15.2 g (150.0 mmol) of triethylamine in 40 ml of tetrahydrofuran was added. After refluxing overnight, the solvent was stripped. The residue was partitioned between water and methylene chloride. The organic phase was washed with 1N hydrochloric acid followed by saturated sodium bicarbonate, then dried and evaporated. The residue was crystallized from hexane to provide 10.4 g (41.2 mmol, 94%) of 2-hydroxy-3-bromo-5-(1,1 dimethylethyl)benzonitrile; mp 69°-71° C.

Workup

  1. temperaturewas cooled in an ice-water bath
  2. temperatureAfter refluxing overnight
  3. customThe residue was partitioned between water and methylene chloride
  4. washThe organic phase was washed with 1N hydrochloric acid
  5. customdried
  6. customevaporated
  7. customThe residue was crystallized from hexane

Sources & evidence

ORD record
ord-f6599463d6544ecf83999a565571ee36
Source dataset
uspto-grants-1990_08
Patent number
US04952583

Reaction notes

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