Phenol → 2-(p-Fluorophenyl)-4-thiocyanato-6-isopropylphenol

HRID 487358Notes

Reaction equation

HRID 487358 reaction equation
[S-:1][C:2]#[N:3].[Na+].[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH:18]([CH3:20])[CH3:19])[C:13]=2[OH:21])=[CH:8][CH:7]=1.BrBr.C1(O)C=CC=CC=1>CO.C1(C)C=CC=CC=1.C1CCCCC1>[F:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:17]=[C:16]([S:1][C:2]#[N:3])[CH:15]=[C:14]([CH:18]([CH3:19])[CH3:20])[C:13]=2[OH:21])=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 996PhenolHCID 24408BromineHCID 516871Sodium thiocyanateHCID 146639662-(p-Fluorophenyl)-6-isopropylphenol

Product 1

HCID 146639782-(p-Fluorophenyl)-4-thiocyanato-6-isopropylphenol

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 21910790Toluene cyclohexaneSolvent

Procedure

A suspension of 70.9 g (838 mmol, 5.0 equivalents) of sodium thiocyanate in 200 ml of methanol was stirred at room temperature for 20 min. 40.0 9 (173.8 mmol, 1.0 equiv.) of 2-(p-fluorophenyl)-6-isopropylphenol were added and the mixture was stirred for 20 minutes. 14.32 ml (277.8 mmol, 1.6 equiv.) of bromine were dissolved in 50 ml of methanol (exothermic) and this solution was added dropwise at 15°-20° C. to the above reaction solution during the course of 20 minutes. The reaction mixture turned yellow and the phenol dissolved completely. The reaction mixture was stirred for 30 min. TLC (toluene/cyclohexane 1:1) showed complete conversion of the starting material (Rf =0.54). In addition to the title compound (Rf =0. 32), only a small amount of the corresponding para-bromo compound, which cochromatographed with the starting material (Rf =0. 54), was obtained as an impurity, but was able to be differentiated owing to different coloration. The reaction mixture was poured onto 400 g of ice/400 ml of 2N hydrochloric acid and extracted using 4×200 ml of toluene. The extracts were washed with aqueous sodium sulfite solution, filtered, washed with saturated sodium chloride solution, dried and concentrated in vacuo.

Workup

  1. stirringthe mixture was stirred for 20 minutes
  2. additionthis solution was added dropwise at 15°-20° C. to the above reaction solution during the course of 20 minutes
  3. stirringThe reaction mixture was stirred for 30 min

Sources & evidence

ORD record
ord-c913922c29c740648d4b37451b121fa6
Source dataset
uspto-grants-1994_03
Patent number
US05294724

Reaction notes

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