Water → 4-(Chloromethyl)-1-fluoro-2-phenoxybenzene

HRID 1639234Notes

Reaction equation

HRID 1639234 reaction equation
S(Cl)([Cl:3])=O.[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12]O)=[CH:8][C:7]=1[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>N1C=CC=CC=1.C(OCC)C>[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][Cl:3])=[CH:8][C:7]=1[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 12874224(4-Fluoro-3-phenoxyphenyl)methanol

Product 1

HCID 135636494-(Chloromethyl)-1-fluoro-2-phenoxybenzeneYield 92%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

In a dry flask were placed in succession 5 mL of diethyl ether, 1.21 g (0.0102 mole) of thionyl chloride, and one drop of pyridine. A solution of 1.85 g (0.0085 mole) of (4-fluoro-3-phenoxyphenyl)methyl alcohol in 5 mL of diethyl ether was added dropwise to the reaction mixture. Upon completion of addition, the reaction mixture was heated at reflux for one hour. After being cooled to room temperature, 10 mL of water was added slowly to the reaction mixture. The phases were separated. Twice the aqueous phase was extracted with 15 mL of diethyl ether, and these extracts were combined with the organic phase. The latter was washed successively twice with 10 mL of a saturated aqueous solution of sodium chloride, once with 10 mL of an aqueous solution of sodium bicarbonate, and twice with the saturated aqueous solution of sodium chloride. After being dried over anhydrous sodium sulfate and being filtered, the solvent was evaporated under reduced pressure, leaving 1.85 g of (4-fluoro-3-phenoxyphenyl)methyl chloride as a light yellow liquid. The nmr and ir spectra were consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux for one hour
  4. customThe phases were separated
  5. extractionTwice the aqueous phase was extracted with 15 mL of diethyl ether
  6. washThe latter was washed successively twice with 10 mL of a saturated aqueous solution of sodium chloride, once with 10 mL of an aqueous solution of sodium bicarbonate
  7. dry with materialAfter being dried over anhydrous sodium sulfate
  8. filtrationbeing filtered
  9. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4179d131ced24eb085c4ffae383a2232
Source dataset
uspto-grants-1989_11
Patent number
US04883789

Reaction notes

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