Boron Trichloride → (4-Fluorophenyl)[2-hydroxy-5-(2,6-dimethyl-4-nitrophenoxy)phenyl]methanone

HRID 1609726Notes

Reaction equation

HRID 1609726 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[C:14]([O:16][C:17]3[C:22]([CH3:23])=[CH:21][C:20]([N+:24]([O-:26])=[O:25])=[CH:19][C:18]=3[CH3:27])[CH:13]=[CH:12][C:11]=2[O:28]C)=[O:9])=[CH:4][CH:3]=1.B(Cl)(Cl)Cl>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:10]2[CH:15]=[C:14]([O:16][C:17]3[C:22]([CH3:23])=[CH:21][C:20]([N+:24]([O-:26])=[O:25])=[CH:19][C:18]=3[CH3:27])[CH:13]=[CH:12][C:11]=2[OH:28])=[O:9])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 10046205(4-Fluorophenyl)[2-methoxy-5-(2,6-dimethyl-4-nitrophenoxy)phenyl]methanone

Product 1

HCID 9999865(4-Fluorophenyl)[2-hydroxy-5-(2,6-dimethyl-4-nitrophenoxy)phenyl]methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5.12 g (13.0 mmol) of (4-fluorophenyl)[2-methoxy-5-(2,6-dimethyl-4nitrophenoxy) phenyl]methanone in 100 ml methylene chloride is chilled in an ice bath and 40 ml (40 mmol) of 1.0 M boron trichloride in methylene chloride is gradually added. The solution is stirred at room temperature overnight, then poured into 300 ml of ice water and stirred 2 hours. The organic layer is separated, washed with 5% aqueous sodium carbonate, water, dried (CaSO4) and evaporated. The residue is recrystallized from ethanol to give (4-fluorophenyl)[2-hydroxy-5-(2,6-dimethyl-4 nitrophenoxy)phenyl]methanone, m.p. 148°-150°.

Workup

  1. stirringstirred 2 hours
  2. customThe organic layer is separated
  3. washwashed with 5% aqueous sodium carbonate, water
  4. dry with materialdried (CaSO4)
  5. customevaporated
  6. customThe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-9a4dff1106ac4cfcbcc86c89f6b1961e
Source dataset
uspto-grants-1995_03
Patent number
US05401772

Reaction notes

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