Water → HCID 10881471、化合物

HRID 1468482ノート

反応式

HRID 1468482 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 10881471HCID 10881471、化合物収率 51%

試薬・触媒・溶媒 1

HCID 10541Trimethyl Phosphate溶媒2 回

反応条件

温度
5 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-0559a113a5a643eda2b6ed6785629cce
出典データセット
uspto-grants-2015_04
特許番号
US09000108B2

反応ノート

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