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

HRID 1710003ノート

反応式

HRID 1710003 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5190e2e7c062499db417b181bb149ddd
出典データセット
uspto-grants-1990_08
特許番号
US04952583

反応ノート

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