Hydrochloric Acid → 2,2'-Diamino-4,4'-dibromobiphenyl

HRID 1160598

反応式

HRID 1160598 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][C:9]=2[N+:15]([O-])=O)=[C:4]([N+:18]([O-])=O)[CH:3]=1.Cl.[Sn].[OH-].[Na+]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([NH2:18])[C:5]([C:8]2[C:9]([NH2:15])=[CH:10][C:11]([Br:14])=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5352426Tin atomHCID 100466484,4'-Dibromo-2,2'-dinitro-1,1'-biphenyl

生成物 1

HCID 112215382,2'-Diamino-4,4'-dibromobiphenyl

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
100 °C

実験手順

To a solution of 15 (11.0 g, 27.4 mmol) in 135 mL of absolute ethanol was added 32% w/w aqueous HCl (78.0 mL). Tin powder (13.0 g, 108.5 mmol) was then added in portions over 10 min, and the reaction mixture was heated to reflux at 100° C. for 2 h. After cooling, the mixture was poured into ice water (400 mL) and then made alkaline with 20% w/w aqueous NaOH solution until the pH was 9.0. The product was next extracted with diethyl ether and the organic layer was washed with brine, dried over anhydrous Na2SO4, filtered, and then evaporated to dryness to give pure product as light-brown crystals that could be used without further purification (8.6 g, 92%). 1H NMR (CDCl3): δ 6.92 (6H, s), 3.78 (4H, br s, NH2) ppm; 13C NMR (CDCl3): δ 118.2, 121.9, 122.1, 122.8, 132.4, 145.3 ppm; m.p. 118-119° C.

後処理

  1. temperaturethe reaction mixture was heated
  2. temperatureAfter cooling
  3. extractionThe product was next extracted with diethyl ether
  4. washthe organic layer was washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customto give pure product as light-brown crystals that
  9. customcould be used without further purification (8.6 g, 92%)

出典と根拠

ORDレコード
ord-8fa31fa0f0344d419ab93ce0ff3752a2
出典データセット
uspto-grants-2010_10
特許番号
US07816480B2

関連ノート

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