Boron tribromide → HCID 57443304, compound

HRID 2261782Notes

Reaction equation

HRID 2261782 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([O:10]C)[CH:7]=[CH:6][C:5]=1[CH2:12][CH2:13][CH3:14].B(Br)(Br)Br>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:5]=1[CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 574433035-Methoxy-2-propyl-benzoic acid methyl ester

Product 1

HCID 57443304HCID 57443304, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a −78° C. solution of 5-Methoxy-2-propyl-benzoic acid methyl ester (350 mg, 1.68 mmol) in DCM (18 mL) is added boron tribromide (840 μL, 8.40 mmol, 1.0 M in DCM) dropwise. The reaction mixture is warmed to room temperature overnight. The reaction mixture is quenched by the dropwise addition of MeOH and is stirred at room temperature for 30 min. The reaction is concentrated and the residue is partitioned between EtOAc and water. The aqueous layer is extracted with EtOAc and the combined organic layers are washed with brine, dried (MgSO4), filtered, concentrated, and chromatographed (0% to 20% EtOAc/Hex) to yield the title compound (274 mg, 84%) 1H NMR (400 MHz, CDCl3) δ 7.34 (d, 1H, J=2.6 Hz), 7.11 (d, 1H, J=8.4 Hz), 6.92 (dd, 1H, J=8.4, 3.1 Hz), 6.92 (dd, 1H, J=8.4, 3.1 Hz), 3.88 (s, 3H), 2.87-2.81 (m, 2H), 1.63-1.52 (m, 2H), 0.94 (t, 3H, J=7.3 Hz).

Workup

  1. customThe reaction mixture is quenched by the dropwise addition of MeOH
  2. concentrationThe reaction is concentrated
  3. customthe residue is partitioned between EtOAc and water
  4. extractionThe aqueous layer is extracted with EtOAc
  5. washthe combined organic layers are washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customchromatographed (0% to 20% EtOAc/Hex)

Sources & evidence

ORD record
ord-2e796350ba12481fa0f18d8268621f7a
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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