2-(Benzyloxy)-5-fluorobenzaldehyde → (+/-)-3-(2-benzyloxy-5-fluoro-phenyl)-3H-isobenzofuran-1-one

HRID 2036235Notes

Reaction equation

HRID 2036235 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:10]=1[CH:11]=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:10]=1[CH:11]1[C:7]2[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:1](=[O:8])[O:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 107281542-(Benzyloxy)-5-fluorobenzaldehyde

Product 1

HCID 66654413(+/-)-3-(2-benzyloxy-5-fluoro-phenyl)-3H-isobenzofuran-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To the Grignard Solution A cooled to −78° C., a solution of 2-benzyloxy-5-fluoro-benzaldehyde (879 mg, 3.82 mmol, 1.0 eq.) in THF (10 mL) was added dropwise. The mixture was stirred at −78° C. for 1 hour and further at r.t. for 18 hours. The reaction was carefully quenched with 1M aq. NH4Cl soln. (50 mL) and AcOEt (100 mL) was added. The resulting suspension was filtered through celite and the filter cake was rinsed with water and AcOEt. The layers were separated and the aq. phase was extracted with AcOEt (2×150 mL). The comb. org. phases were washed with sat. aq. NaCl soln. (1×100 mL), dried over MgSO4, and concentrated in vacuo. The residue was purified by flash master (column: 100 g, flow: 45 mL/min, Heptane to Heptane+45% AcOEt) to yield (±)-3-(2-benzyloxy-5-fluoro-phenyl)-3H-isobenzofuran-1-one as a white solid.

Workup

  1. customThe reaction was carefully quenched with 1M aq. NH4Cl soln
  2. addition(50 mL) and AcOEt (100 mL) was added
  3. filtrationThe resulting suspension was filtered through celite
  4. washthe filter cake was rinsed with water and AcOEt
  5. customThe layers were separated
  6. extractionthe aq. phase was extracted with AcOEt (2×150 mL)
  7. washphases were washed with sat. aq. NaCl soln
  8. dry with material(1×100 mL), dried over MgSO4
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by flash master (column: 100 g, flow: 45 mL/min, Heptane to Heptane+45% AcOEt)

Sources & evidence

ORD record
ord-f7284dfff6dc40c4975be04e66e91ea6
Source dataset
uspto-grants-2013_11
Patent number
US08575158B2

Reaction notes

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