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

HRID 866010Notes

Reaction equation

HRID 866010 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-4-nitrophenoxy)phenyl]methanone in 100 ml methylene chloride is chilled in an ice bath and 40 ml (40 mmol) of 1.0M boron trichloride in methylene chloride is gradually added. The solution is stirred at room temperature overnight, then pour 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-134010f60875443389718485121ce521
Source dataset
uspto-grants-1996_10
Patent number
US05569674

Reaction notes

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