Diisopropylethylamine → HCID 86676268, compound

HRID 2038709Notes

Reaction equation

HRID 2038709 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-0a7fd089991d429d8a0f8fb760ed911b
Source dataset
uspto-grants-2013_11
Patent number
US08575336B2

Reaction notes

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