Diisopropylethylamine → HCID 86676268, compound

HRID 340059Notes

Reaction equation

HRID 340059 reaction equation
[Br:1][C:2]1[C:7]([CH2:8][CH3:9])=[CH:6][C:5]([OH:10])=[C:4]([F:11])[CH:3]=1.CCN(C(C)C)C(C)C.[CH3:21][Si:22]([CH2:25][CH2:26][O:27][CH2:28]Cl)([CH3:24])[CH3:23]>C(Cl)Cl>[Br:1][C:2]1[C:7]([CH2:8][CH3:9])=[CH:6][C:5]([O:10][CH2:28][O:27][CH2:26][CH2:25][Si:22]([CH3:24])([CH3:23])[CH3:21])=[C:4]([F:11])[CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 71238161HCID 71238161, compound

Product 1

HCID 86676268HCID 86676268, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromo-5-ethyl-2-fluoro-phenol (Preparation 3, 80 g, 365 mmol) in DCM (1 L) was added DIPEA (70 mL, 401 mmol) and SEM-Cl (71 mL, 401 mmol). The resulting solution was stirred at room temperature for 18 hours. The reaction mixture was washed with water (1 L), dried over MgSO4 and concentrated in vacuo to yield the crude product. This material was purified by silica gel chromatography eluting with 30% DCM in heptane to give the title compound as a pale yellow oil (109.8 g, 86%).

Workup

  1. washThe reaction mixture was washed with water (1 L)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customto yield the crude product
  5. customThis material was purified by silica gel chromatography
  6. washeluting with 30% DCM in heptane

Sources & evidence

ORD record
ord-3b3b7f2f0ac8404aa146bfb8e6b6d7fe
Source dataset
uspto-grants-2014_11
Patent number
US08895544B2

Reaction notes

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