Water → HCID 10881471, 화합물

HRID 1468482노트

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HRID 1468482 반응식
[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:4][C:3]=1[OH:12].S(Cl)([Cl:16])(=O)=O.O>P(OC)(OC)(OC)=O>[Cl:16][C:6]1[C:5]([C:8]([CH3:9])([CH3:11])[CH3:10])=[CH:4][C:3]([OH:12])=[C:2]([I:1])[CH:7]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 24648Sulfuryl chlorideHCID 117478025-tert-Butyl-2-iodophenol

생성물 1

HCID 10881471HCID 10881471, 화합물수율 51%

시약·촉매·용매 1

HCID 10541Trimethyl Phosphate용매2회

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온도
5 °C

실험 절차

To 35 mL of trimethyl phosphate (TMP) at 0° C. to 10° C. add 2-iodo-5-(1,1-dimethylethyl)phenol (6.61 g, 23.95 mmol, Preparation 42). To this solution add dropwise over the period of one minute sulfuryl chloride (2.0 mL, 24.67 mmol) in 35 mL of TMP, and then stir the resulting mixture for 30 minutes still at 0-10° C. To the reaction mixture add 130 mL of water, and then extract the resulting quenchate into CH2Cl2. Dry combined organic phases over anhydrous MgSO4, filter through silica gel, and concentrate filtrate. Purify residue by flash chromatography using 5% ethyl acetate in hexanes to give 3.79 g (51%) of 4-chloro-2-iodo-5-(1,1-dimethylethyl)phenol as a golden oil. 1H NMR (400 MHz, CDCl3) δ 7.58 (s, 1H), 7.05 (s, 1H), 5.21 (s, 1H), 1.43 (s, 9H). 13C NMR (101 MHz, CDCl3) δ 153.73, 149.02, 139.63, 125.69, 114.23, 81.61, 77.32, 76.68, 36.03, 29.29. MS m/e 310.

후처리

  1. extractionextract the resulting quenchate into CH2Cl2
  2. customDry
  3. filtrationfilter through silica gel
  4. concentrationconcentrate filtrate

출처 및 근거

ORD 기록
ord-0559a113a5a643eda2b6ed6785629cce
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09000108B2

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