Trimethylsilyl iodide → Methyl 3-bromo-5-(3-hydroxypropyl)-4-methylbenzoate

HRID 337653Notes

Reaction equation

HRID 337653 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH2:13][CH2:14][CH2:15][O:16]C)[C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6].I[Si](C)(C)C>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH2:13][CH2:14][CH2:15][OH:16])[C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 66895990Methyl 3-bromo-5-(3-methoxypropyl)-4-methylbenzoate

Product 1

HCID 66895715Methyl 3-bromo-5-(3-hydroxypropyl)-4-methylbenzoate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a chloroform (0.1 M) solution of methyl 3-bromo-5-(3-methoxypropyl)-4-methylbenzoate (1 eq., Amine 88, Step 2) was added iodotrimethylsilane (3 eq.). The resulting red solution was stirred at RT in darkness for 18 h. The reaction was quenched with methanol before the volatiles were removed in vacuo. The resulting residue was then taken up in ether, washed sequentially with 10% aq. HCl, 1 N aq. NaOH, water and brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product by way of flash chromatography (SiO2, Hex→3:7 (v/v) Hex:EtOAc) afforded the title compound as a pale yellow oil.

Workup

  1. customThe reaction was quenched with methanol before the volatiles
  2. customwere removed in vacuo
  3. washwashed sequentially with 10% aq. HCl, 1 N aq. NaOH, water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo
  7. customPurification of the crude product by way of flash chromatography (SiO2, Hex→3:7 (v/v) Hex:EtOAc)

Sources & evidence

ORD record
ord-028327b65cdd4ef68a0269f358822a8f
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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