Isopropanol → 4-Bromo-1-chloro-2-isopropoxybenzene

HRID 270778Notes

Reaction equation

HRID 270778 reaction equation
[C:1]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:6]=CC=C[CH:2]=1.CCOC(/N=N/C(OCC)=O)=O.C(O)(C)C.[Br:36][C:37]1[CH:38]=[C:39]([OH:44])[C:40]([Cl:43])=[CH:41][CH:42]=1>C(Cl)Cl>[Br:36][C:37]1[CH:42]=[CH:41][C:40]([Cl:43])=[C:39]([O:44][CH:1]([CH3:6])[CH3:2])[CH:38]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 8203925-Bromo-2-chlorophenolHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 210710294-Bromo-1-chloro-2-isopropoxybenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1.70 g (6.5 mmol) of triphenylphosphine in 25 mL of CH2Cl2 at 0° C. was added 1.14 g (6.5 mmol) of diethylazodicarboxylate. After 10 minutes, 390 mg (6.5 mmol) of isopropanol was added, followed rapidly by 1.03 g (5.0 mmol) of 3-Bromo-6-chlorophenol. The reaction was complete within three hours, and was partitioned between ether and water. The phases were separated, and the ether phase was diluted with hexanes and washed twice with 10% aqueous methanol and once with brine. The ether/hexanes phase was dried over Na2SO4, filtered, and concentrated in vacuo to yield product as a clear oil.

Workup

  1. waitThe reaction was complete within three hours
  2. customwas partitioned between ether and water
  3. customThe phases were separated
  4. additionthe ether phase was diluted with hexanes
  5. washwashed twice with 10% aqueous methanol and once with brine
  6. dry with materialThe ether/hexanes phase was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto yield product as a clear oil

Sources & evidence

ORD record
ord-dd49bab31c5d4adeb3d505715e9c6f13
Source dataset
uspto-grants-2008_11
Patent number
US07449576B1

Reaction notes

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