Boron tribromide → 4-((5-Bromo-2-chlorophenyl)methyl)phenol

HRID 59203

反応式

HRID 59203 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16]CC)=[CH:12][CH:11]=2)[CH:3]=1.B(Br)(Br)Br>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([CH:3]=1)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 99964494-Bromo-1-chloro-2-(4-ethoxy-benzyl)-benzene

生成物 1

HCID 574237514-((5-Bromo-2-chlorophenyl)methyl)phenol収率 77.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 4-bromo-1-chloro-2-(4-ethoxy-benzyl)-benzene (5.0 g, 15.35 mmol) in dichloromethane (20.0 mL) cooled to 0 degrees Celsius under nitrogen was added drop-wise over 30 minutes a 1M solution of boron tribromide in dichloromethane (17.0 mL, 17.0 mmol). After the addition was complete, the reaction was allowed to warm to room temperature overnight (˜16 hours). The reaction was cooled to 0 degrees Celsius and quenched with an aqueous solution of 1N hydrochloric acid. The resulting mixture was stirred for 30 minutes and extracted using dichloromethane. The organic layer was separated and the aqueous layer was extracted two times with dichloromethane. The combined organic layers were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The reaction was purified by flash chromatography over silica gel using the ISCO automated chromatography unit (120 g silica gel column) and eluting with a gradient of 0 to 100% ethyl acetate in heptane. 3.53 g of desired product obtained (77% yield). 1H NMR (400 MHz, METHANOL-d4) delta ppm 3.94 (s, 2 H), 6.70 (d, J=8.6 Hz, 2 H), 6.98 (d, J=8.4 Hz, 2 H), 7.23-7.34 (m, 3 H).

後処理

  1. additionAfter the addition
  2. temperatureThe reaction was cooled to 0 degrees Celsius
  3. customquenched with an aqueous solution of 1N hydrochloric acid
  4. extractionextracted
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted two times with dichloromethane
  7. dry with materialThe combined organic layers were dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe reaction was purified by flash chromatography over silica gel using the ISCO automated chromatography unit (120 g silica gel column)
  11. washeluting with a gradient of 0 to 100% ethyl acetate in heptane

出典と根拠

ORDレコード
ord-ab148d4bf7b741e29c49080569323d99
出典データセット
uspto-grants-2016_09
特許番号
US09439902B2

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