N,N-Diethylaniline → 2-Allyl-6-bromo-4-chlorophenol

HRID 1466614Notes

Reaction equation

HRID 1466614 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:6]=1[Br:12])C=C.C(N(CC)[C:16]1[CH:21]=CC=C[CH:17]=1)C>>[CH2:21]([C:10]1[CH:9]=[C:8]([Cl:11])[CH:7]=[C:6]([Br:12])[C:5]=1[OH:4])[CH:16]=[CH2:17]

Participants

3

Reactant 2

HCID 7061N,N-DiethylanilineHCID 3340901-(Allyloxy)-2-bromo-4-chlorobenzene

Product 1

HCID 548490402-Allyl-6-bromo-4-chlorophenolYield 77.1%

Procedure

A solution of 1-(allyloxy)-2-bromo-4-chlorobenzene (4.122 g, 16.65 mmol) in N,N-diethylaniline (20 mL, 100 mmol) was heated at 200° C. for 15 hours. After cooling to room temperature, the reaction mixture was partitioned between ethyl acetate and 1M aqueous HCl, and the organic layer washed with an additional portion of 1M aqueous HCl and then brine. The organic layer was dried over magnesium sulfate and evaporated in vacuo. The crude product was purified via flash chromatography on silica gel (0 to 20% ethyl acetate in heptanes) to yield 3.1761 g (77%) of 2-allyl-6-bromo-4-chlorophenol as a clear, colorless oil. 1H NMR (400 MHz, CDCl3) δ: 7.33 (d, J=2.4, 1H), 7.07 (d, J=2.3, 1H), 5.94 (ddt, J=16.8, 10.3, 6.6, 1H), 5.53 (s, 1H), 5.18-5.06 (m, 2H) 3.40 (d J=6.6, 2H).

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate and 1M aqueous HCl
  2. washthe organic layer washed with an additional portion of 1M aqueous HCl
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe crude product was purified via flash chromatography on silica gel (0 to 20% ethyl acetate in heptanes)

Sources & evidence

ORD record
ord-a3c2619d796345c3a109c320bc413d35
Source dataset
uspto-grants-2015_04
Patent number
US08999998B2

Reaction notes

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