O-Cresol → 2-Bromo-6-methylphenol

HRID 564456

Reaction equation

HRID 564456 reaction equation
[C:1]1([CH3:8])[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][CH:2]=1.N(C(C)C)C(C)C.C1C(=O)N([Br:23])C(=O)C1.S(=O)(=O)(O)O>C(Cl)Cl.O>[Br:23][C:5]1[CH:4]=[CH:3][CH:2]=[C:1]([CH3:8])[C:6]=1[OH:7]

Participants

7

Reactant 4

HCID 335O-CresolHCID 1118Sulfuric AcidHCID 7912DiisopropylamineHCID 67184N-bromobutanimide

Product 1

HCID 110953292-Bromo-6-methylphenolYield 97.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of o-cresol (20.0 g, 0.19 mol) and iPr2NH (2.63 mL, 18.5 mmol) in CH2Cl2 (500 mL), a solution of NBS (32.9 g, 0.19 mol) in CH2Cl2 (500 mL) was added dropwise over 7 h and the mixture was stirred over night at room temperature. The reaction mixture was acidified to pH=1 with conc. sulfuric acid and water (400 mL). The organic layer was separated, dried with Na2SO4, and concentrated under reduced pressure. 34.6 g of the crude product was obtained (yield: 97%). 1H NMR (400 MHz, CDCl3) δ 2.30 (s, 3 H), 5.54 (s, 2 H), 6.71 (t, J=7.6 Hz, 1 H), 7.05 (d, J=7.6 Hz, 1 H), 7.28 (d, J=8.0 Hz, 1 H).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried with Na2SO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1fdcf9ffd2eb471289d43a8fb596e30a
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Linked notes

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