4-tert-Butylphenol → 4-tert-Butyl-2-chlorophenol

HRID 855250Notes

Reaction equation

HRID 855250 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Cl:19])C(=O)C1>C(#N)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([OH:11])=[C:9]([Cl:19])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 73934-tert-ButylphenolHCID 31398Chlorosuccinimide2×

Product 1

HCID 73804-tert-Butyl-2-chlorophenolYield 81%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.50 g (10 mmol) of 4-tert.-butyl phenol were dissolved in 40 ml acetonitrile. 1.34 g (10 mmol) of NCS were added and the reaction mixture was stirred at rt over night. The reaction mixture was heated for 1.5 h to reflux. Then additional 134 mg (1 mmol) of NCS were added and the reaction mixture was heated to reflux for 2 h. The solvent was evaporated and the residue was stirred with diethyl ether for 15 min. The solid was filtered off and the filtrate was evaporated. The residue was purified by column chromatography (100 silica gel, DCM) to yield 1.49 g (81%) of 4-tert.-butyl-2-chloro-phenol as a colorless viscous oil. 1H NMR (DMSO-d6, 300 MHz): δ 9.85 (s, 1H), 7.26 (s, 1H), 7.14 (d, 2H), 6.88 (d, 2H), 1.22 (s, 9H).

Workup

  1. temperatureThe reaction mixture was heated for 1.5 h
  2. temperatureto reflux
  3. temperaturethe reaction mixture was heated
  4. temperatureto reflux for 2 h
  5. customThe solvent was evaporated
  6. stirringthe residue was stirred with diethyl ether for 15 min
  7. filtrationThe solid was filtered off
  8. customthe filtrate was evaporated
  9. customThe residue was purified by column chromatography (100 silica gel, DCM)

Sources & evidence

ORD record
ord-d86497839366478bbf61386a4be50162
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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