Bromine → 5-tert-Butyl-2-methyl-4-thiocyanato-phenol

HRID 356500ノート

反応式

HRID 356500 の反応式
[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH3:12])=[C:9]([OH:11])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[S:13](C#N)[C:14]#[N:15].[Na].[Br-].[Na+].BrBr>CO>[C:1]([C:5]1[C:6]([S:13][C:14]#[N:15])=[CH:7][C:8]([CH3:12])=[C:9]([OH:11])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 24408BromineHCID 798455-tert-Butyl-o-cresolHCID 253881Sodium BromideHCID 86753328CID 86753328

生成物 1

HCID 105609555-tert-Butyl-2-methyl-4-thiocyanato-phenol

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
40 °C

実験手順

In a 5 L flask were placed 350 g (2.13 mol) of 5-tert-butyl-2-methyl-phenol, sodium thiocyanide (555 g, 6.85 mol) and MeOH (1400 mL), and the resulting mixture cooled to 7° C. A solution of sodium bromide (214 g, 2.08 mol), bromine (126 mL, 2.38 mol), and MeOH (1800 mL) was added slowly and the temperature raised to 40° C. over a period of 30 minutes. The precipitants were filtered and the filtrate concentrated by half. Saturated sodium carbonate (3.5 L) and H2O (4.5 L) were added. The mixture was extracted with EtOAc (3 L), and the organic layers were combined and concentrated. To this residue were added t-butylmethyl ether (500 mL) and hexanes (500 mL), and the mixture was allowed to stand for 17 hours at -5° C. The precipitants were filtered to give the title compound, m.p. 99°-102° C. 1H NMR (CDCl3) δ 1.46 (s, 9 H), 2.22 (s, 3 H), 5.01 (s, 1 H), 6.89 (s, 1 H), 7.49 (s, 1 H).

後処理

  1. customIn a 5 L flask were placed
  2. filtrationThe precipitants were filtered
  3. concentrationthe filtrate concentrated by half
  4. additionSaturated sodium carbonate (3.5 L) and H2O (4.5 L) were added
  5. extractionThe mixture was extracted with EtOAc (3 L)
  6. concentrationconcentrated
  7. additionTo this residue were added t-butylmethyl ether (500 mL) and hexanes (500 mL)
  8. filtrationThe precipitants were filtered

出典と根拠

ORDレコード
ord-aefea9b903b04ba99103150098733d61
出典データセット
uspto-grants-1998_11
特許番号
US05834506

反応ノート

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