2,7-Naphthalenediol → 7-Bromo-2-naphthol

HRID 1760613

反応式

HRID 1760613 の反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]Br.[OH:22][C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][C:27](O)=[CH:28][CH:29]=2)[CH:24]=1>CC#N>[Br:20][C:27]1[CH:26]=[C:25]2[C:30]([CH:31]=[CH:32][C:23]([OH:22])=[CH:24]2)=[CH:29][CH:28]=1

参加物

5

反応物 3

HCID 113972,7-NaphthalenediolHCID 11776TriphenylphosphineHCID 24408Bromine

生成物 1

HCID 6138277-Bromo-2-naphthol収率 43%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

反応条件

温度
10 °C

実験手順

Triphenyl phosphine (89.7 g, 0.342 mol) and acetonitrile (350 mL) were combined in a 1-L flask under N2 atmosphere. The mixture was cooled to 10° C. Bromine (17.6 mL, 0.342 mol) was added dropwise over 10 minutes. The cooling bath was removed and 2,7-dihydroxynaphthalene (50.0 g, 0.312 mol) was added along with 350 mL of CH3CN rinse. The resulting yellow tan mixture was heated at reflux for 3 hours. Acetonitrile was distilled off using a water aspirator over 2 hours resulting in a grayish white solid. The solid was heated to 280° C. over 30 minutes giving a black liquid. The liquid was heated to 310° C. over 20 minutes and the temperature was maintained at 310° C. for an additional 15 minutes until gas evolution ceased. The black mixture was cooled to room temperature. Chromatography yielded 34.5 g of the intermediate title compound as an off-white solid which was 87% pure by HPLC (43% yield).

後処理

  1. customThe cooling bath was removed
  2. washrinse
  3. temperatureThe resulting yellow tan mixture was heated
  4. temperatureat reflux for 3 hours
  5. distillationAcetonitrile was distilled off
  6. customresulting in a grayish white solid
  7. temperatureThe solid was heated to 280° C. over 30 minutes
  8. customgiving a black liquid
  9. temperatureThe liquid was heated to 310° C. over 20 minutes
  10. temperaturethe temperature was maintained at 310° C. for an additional 15 minutes until gas evolution
  11. temperatureThe black mixture was cooled to room temperature

出典と根拠

ORDレコード
ord-573ac339c38149fe8cf5990f4a3211f8
出典データセット
uspto-grants-2005_01
特許番号
US06844344B2

関連ノート

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