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

HRID 356500노트

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HRID 356500 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매2회

반응 조건

온도
40 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-aefea9b903b04ba99103150098733d61
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05834506

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