6-Bromo-1,3-dihydroisobenzofuran-1-ol → (5-Bromo-2-(hydroxymethyl)phenyl)(4-ethylphenyl)methanol

HRID 576377Notes

Reaction equation

HRID 576377 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][O:7][CH:8]2[OH:11])=[CH:4][CH:3]=1.[CH2:12]([C:14]1[CH:19]=[CH:18][C:17]([Mg]Br)=[CH:16][CH:15]=1)[CH3:13]>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][OH:7])=[C:9]([CH:8]([C:17]2[CH:18]=[CH:19][C:14]([CH2:12][CH3:13])=[CH:15][CH:16]=2)[OH:11])[CH:10]=1

Participants

4

Reactant 2

HCID 136136836-Bromo-1,3-dihydroisobenzofuran-1-olHCID 178436501HCID 178436501, compound

Product 1

HCID 68233732(5-Bromo-2-(hydroxymethyl)phenyl)(4-ethylphenyl)methanolYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Step 2) To a solution of compound 145 (2.1 g, 9.77 mmol) in tetrahydrofuran (40.0 mL) was slowly added 4-ethylphenylmagnesium bromide (39 mL, 0.5M solution in THF) at 0° C., and the reaction mixture was stirred for 12 h at room temperature. The resulting mixture was quenched with sat. NH4Cl, diluted with EtOAc and washed with brine. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The crude was purified by silica gel column chromatography to provide (5-bromo-2-(hydroxymethyl)phenyl)(4-ethylphenyl)methanol (146, 1.53 g, 49%) as yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.50 (d, J=2.0 Hz, 1H), 7.42 (dd, J=8.0, 2.0 Hz, 1H), 7.26-7.17 (m, 5H), 5.97 (s, 1H), 4.58 (d, J=12.8 Hz, 1H), 4.43 (d, J=12.4 Hz, 1H), 2.65 (q, J=7.6 Hz, 2H), 1.23 (t, J=7.6 Hz, 3H).

Workup

  1. customat 0° C.
  2. customThe resulting mixture was quenched with sat. NH4Cl
  3. additiondiluted with EtOAc
  4. washwashed with brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2297e592f91d4eccbf54cd159294b9bc
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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