Hydrochloric Acid → 106969-10-2

HRID 2309320Notes

Reaction equation

HRID 2309320 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[OH:12].[OH-].[Na+].Cl[CH:16]([F:18])[F:17].Cl>ClCCl.O.C(O)(C)C>[Cl:1][C:2]1[C:3]([O:12][CH:16]([F:18])[F:17])=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([F:8])[CH:7]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6372ChlorodifluoromethaneHCID 14798Sodium Hydroxide2×HCID 158655Phenol, 2-chloro-4-fluoro-5-nitro-

Product 1

HCID 13961080106969-10-2

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

To 0.53 g of 2-chloro-4-fluoro-5-nitrophenol XV-1 were added 3 ml of isopropanol, 3 ml of water and 0.72 g of sodium hydroxide, and the resultant mixture was heated at 50° to 60° C. while introducing chlorodifluoromethane gas for 4 hours. The mixture was stirred for 4 hours and during that period mixed twice with 0.50 g of sodium hydroxide at intervals of 1.5 hours. After cooling, the reaction mixture was neutralized with 2N hydrochloride acid and shaken with dichloromethane. The dichloromethane layer was dried and concentrated. The residue was chromatographed on a column of silica gel, eluting with n-hexane-ethylacetate (100:5 v/v). The eluate was concentrated to give 0.24 g of the titled compound XII-1.

Workup

  1. temperatureAfter cooling
  2. dry with materialThe dichloromethane layer was dried
  3. concentrationconcentrated
  4. customThe residue was chromatographed on a column of silica gel
  5. washeluting with n-hexane-ethylacetate (100:5 v/v)
  6. concentrationThe eluate was concentrated

Sources & evidence

ORD record
ord-1dbda0cb99e14ed781510cc2f5469569
Source dataset
uspto-grants-1987_09
Patent number
US04695312

Reaction notes

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