Water → HCID 25023955, compound

HRID 646194Notes

Reaction equation

HRID 646194 reaction equation
[Cl:1][C:2]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][C:6]=1[O:13]C.O>ClCCl>[Cl:1][C:2]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][C:6]=1[OH:13]

Participants

4

Reactant 2

HCID 962WaterHCID 686144854-(2,4-Dichlorophenoxy)-3-methoxybenzonitrile

Product 1

HCID 25023955HCID 25023955, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

56 g of 4-(2,4-dichlorophenoxy)-3-methoxybenzonitrile are dissolved in 120 ml of dichloromethane. At 0°, a 1M solution of borontribromide in dichloromethane is added slowly in 4 portions of 6 ml each. The reaction mixture is then stirred for 2 days at room temperature. After renewed cooling to 0°, water is added carefully until no reaction is observed any more. The reaction mixture is then washed with water, a saturated aqueous solution of sodium bicarbonate and finally with brine. The organic phase is dried over magnesium sulfate and evaporated under vacuum. The residue is recrystallized from ether/hexane to yield 4-(2,4-dichlorophenoxy)-3-hydroxybenzonitrile.

Workup

  1. temperatureAfter renewed cooling to 0°
  2. washThe reaction mixture is then washed with water
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. customevaporated under vacuum
  5. customThe residue is recrystallized from ether/hexane

Sources & evidence

ORD record
ord-fa763afd12764675bb74dee74e40ec98
Source dataset
uspto-grants-2010_04
Patent number
US07705047B2

Reaction notes

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