Triethylamine → 2-(T-Butyldimethylsilyloxy)-4-bromoanisole

HRID 1810164Notes

Reaction equation

HRID 1810164 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][CH3:10])=[C:6]([OH:8])[CH:7]=1.C(N(CC)CC)C.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][CH3:10])=[C:6]([CH:7]=1)[O:8][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 1422285-Bromo-2-methoxyphenol

Product 1

HCID 109800492-(T-Butyldimethylsilyloxy)-4-bromoanisoleYield 100%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromo-2-methoxy-phenol (3.5 g, 17.2 mmol) dissolved in methylene chloride (50 mL) are added triethylamine (2.08 g, 20.6 mmol) and 4-dimethylaminopyridine (0.15 g, 0.86 mmol). Then tert-butyldimethylsilyl chloride is added slowly and the reaction mixture is stirred at room temperature for 16 h. The reaction is quenched with 10% of citric acid, and then the organic layer is washed with saturated sodium bicarbonate solution, a saturated sodium chloride solution, dried with magnesium sulfate, and concentrated in vacuo. Purification by silica gel chromatography (15% ethyl acetate-hexane) provides 5.6 g (100%) of the title compound as a colorless oil. 1H NMR (CDCl3): δ 6.82 (m, 2H), 6.58 (d, J=9 Hz, 1H), 3.74 (s, 3H), 0.95 (s, 9H), 0.05 (s, 6H).

Workup

  1. customThe reaction is quenched with 10% of citric acid
  2. washthe organic layer is washed with saturated sodium bicarbonate solution
  3. dry with materiala saturated sodium chloride solution, dried with magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification by silica gel chromatography (15% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-b336f220965f4b3fbdaf1a1403298fe5
Source dataset
uspto-grants-2013_01
Patent number
US08362063B2

Reaction notes

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