Hydrochloric Acid → 2-Iodo-5-(trifluoromethyl)phenol

HRID 1906518Notes

Reaction equation

HRID 1906518 reaction equation
[H-].[Na+].[F:3][C:4]([F:13])([F:12])[C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1.[I:14]I.Cl>CCCCCC.C1(C)C=CC=CC=1.CCOCC>[I:14][C:8]1[CH:9]=[CH:10][C:5]([C:4]([F:12])([F:13])[F:3])=[CH:6][C:7]=1[OH:11]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 73763-(Trifluoromethyl)phenolHCID 24758Sodium hydride2×

Product 1

HCID 138235382-Iodo-5-(trifluoromethyl)phenolYield 102.1%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

To a round bottom flask under N2 was added 14.2 g (0.296 mole) of sodium hydride, 50% in oil. The NaH was washed twice with hexane, and 33.15 g (0.205 mole) of m-trifluoromethylphenol in 1 liter of toluene was added. After five minutes 51.9 g (0.205 mole) of iodine was added all at once, and the solution allowed to stir overnight. The reaction was poured into 3N HCl, ether added, and the separated organic layer washed with water, brine and dried with MgSo4. The solvent was evaporated in vacuo to give 60.3 g (100% yield) of 2-iodo-5-trifluoromethylphenol, mp 36°-38° C.

Workup

  1. additionwas added
  2. additionadded
  3. washthe separated organic layer washed with water, brine
  4. customdried with MgSo4
  5. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-eb70b5ed65b748b3924dafad5bc5ddaf
Source dataset
uspto-grants-1987_03
Patent number
US04652584

Reaction notes

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