Isopropanol → 1-Bromo-4-isopropoxy-2-methyl-5-nitro-benzene

HRID 388554Notes

Reaction equation

HRID 388554 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[CH3:13][CH:14](O)[CH3:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[C:5]([O:9][CH:14]([CH3:15])[CH3:13])=[CH:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 234364034-Bromo-5-methyl-2-nitrophenol

Product 1

HCID 597645931-Bromo-4-isopropoxy-2-methyl-5-nitro-benzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-Bromo-5-methyl-2-nitro-phenol from the previous step (0.66 g, 2.84 mmol), 2-propanol (0.262 mL), and triphenylphosphine (894 mg) in 10 mL THF is added diisopropyl asodicarboxylate (0.671 mL) at 22° C. The reaction mixture is concentrated in vacuo. The residue is purified using a SiO2 column (ISCO), affording 1-Bromo-4-isopropoxy-2-methyl-5-nitro-benzene as a bright yellow solid.

Workup

  1. additionis added diisopropyl asodicarboxylate (0.671 mL) at 22° C
  2. concentrationThe reaction mixture is concentrated in vacuo
  3. customThe residue is purified

Sources & evidence

ORD record
ord-d2f95a3d52af4b6e9e0ec1f55d2f097f
Source dataset
uspto-grants-2013_02
Patent number
US08377921B2

Reaction notes

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