Water → HCID 10881471, compound

HRID 1468482Notes

Reaction equation

HRID 1468482 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 10881471HCID 10881471, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 10541Trimethyl PhosphateSolvent2×

Conditions

Temperature
5 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-0559a113a5a643eda2b6ed6785629cce
Source dataset
uspto-grants-2015_04
Patent number
US09000108B2

Reaction notes

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