Triethylamine → 2-Hydroxy-3-bromo-4-chloro-5-(1,1-dimethylethyl)benzonitrile

HRID 1710003노트

반응식

HRID 1710003 반응식
[OH:1][C:2]1[C:10]([Br:11])=[C:9]([Cl:12])[C:8]([C:13]([CH3:16])([CH3:15])[CH3:14])=[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])=[C:9]([Cl:12])[C:8]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:7][C:3]=1[C:4]#[N:5]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 1364045082-Hydroxy-3-bromo-4-chloro-5-(1,1-dimethylethyl)benzaldehyde oxime

생성물 1

HCID 230354212-Hydroxy-3-bromo-4-chloro-5-(1,1-dimethylethyl)benzonitrile수율 87%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A mixture of 2.20 g (7.18 mmol) of 2-hydroxy-3-bromo-4-chloro-5-(1,1-dimethylethyl)benzaldehyde oxime and 3.12 g (14.72 mmol) of trifluoroacetic anhydride in 15 ml of tetrahydrofuran was cooled in an ice-water bath. A solution of 2.18 g (21.54 mmol) of triethylamine in 10 ml of tetrahydrofuran was added After refluxing for 2 hours, the solvent was evaporated and the residue was partitioned between saturated aqueous sodium bicarbonate solution and ether. The organic phase was washed with 1N hydrochloric acid, followed by water and brine. The organic phase was dried and evaporated. The residue was chromatographed on 100 g of silica gel using a gradient from 5:95 to 50:50 (v/v) ether:hexane as eluent. There was obtained 1.80 g (6.23 mmol, 87%) of 2-hydroxy-3-bromo-4-chloro-5-(1,1-dimethylethyl)benzonitrile; mp 105°-107° C.

후처리

  1. temperaturewas cooled in an ice-water bath
  2. temperatureAfter refluxing for 2 hours
  3. customthe solvent was evaporated
  4. customthe residue was partitioned between saturated aqueous sodium bicarbonate solution and ether
  5. washThe organic phase was washed with 1N hydrochloric acid
  6. customThe organic phase was dried
  7. customevaporated
  8. customThe residue was chromatographed on 100 g of silica gel using a gradient from 5:95 to 50:50 (v/v) ether

출처 및 근거

ORD 기록
ord-5190e2e7c062499db417b181bb149ddd
출처 데이터셋
uspto-grants-1990_08
특허 번호
US04952583

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