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

HRID 2206751Notes

Reaction equation

HRID 2206751 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, 0.5 M 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-6c094e21a9154f0789b47492e70175eb
Source dataset
uspto-grants-2016_06
Patent number
US09371303B2

Reaction notes

Loading…