Boron tribromide → 2-[(4-Fluorophenyl)methyl]-4-(2,6-dimethyl-4-nitrophenoxy)phenol

HRID 2256493Notes

Reaction equation

HRID 2256493 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:14]=[C:13]([O:15][C:16]3[C:21]([CH3:22])=[CH:20][C:19]([N+:23]([O-:25])=[O:24])=[CH:18][C:17]=3[CH3:26])[CH:12]=[CH:11][C:10]=2[O:27]C)=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]2[CH:14]=[C:13]([O:15][C:16]3[C:21]([CH3:22])=[CH:20][C:19]([N+:23]([O-:25])=[O:24])=[CH:18][C:17]=3[CH3:26])[CH:12]=[CH:11][C:10]=2[OH:27])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 104074661-[(4-Fluorophenyl)methyl]-2-methoxy-5-(2,6-dimethyl-4-nitrophenoxy)benzene

Product 1

HCID 190301002-[(4-Fluorophenyl)methyl]-4-(2,6-dimethyl-4-nitrophenoxy)phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1.7 g (4.5 mmol) of 1-[(4-fluorophenyl)methyl]-2-methoxy-5-(2,6-dimethyl-4-nitrophenoxy)benzene in 100 ml methylene chloride is added 13.5 ml (13.5 mmol) 1.0N boron tribromide in methylene chloride. The solution is stirred overnight at room temperature, poured into ice water (300 ml) and stirred 1 hour. The organic layer is separated, washed with water, dried (CaSO4) and evaporated. Flash chromatography of the residue gives 2-[(4-fluorophenyl)methyl]-4-(2,6-dimethyl-4-nitrophenoxy)phenol, m.p. 127°-132°.

Workup

  1. stirringstirred 1 hour
  2. customThe organic layer is separated
  3. washwashed with water
  4. dry with materialdried (CaSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-bc878ad7aebd42e1863cfaeca9a93798
Source dataset
uspto-grants-1997_08
Patent number
US05654468

Reaction notes

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