2-Bromo-5-fluorobenzaldehyde → (2-Bromo-5-fluorophenyl)(phenyl)methanol

HRID 469548

Reaction equation

HRID 469548 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:9][C:10]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:11]=1[CH:12]=[O:13]>CCOCC.C1COCC1.CCOC(C)=O>[Br:9][C:10]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:11]=1[CH:12]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[OH:13]

Participants

6

Reactant 2

HCID 27733212-Bromo-5-fluorobenzaldehydeHCID 178418255HCID 178418255, compound

Product 1

HCID 61100031(2-Bromo-5-fluorophenyl)(phenyl)methanolYield 85.4%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of PhMgBr (1M in THF, 2.60 mL, 2.60 mmol) was added dropwise to a −78° C. solution of 2-bromo-5-fluorobenzaldehyde (0.4742 g, 2.336 mmol) in Et2O (5 mL) and THF (1.3 mL), stirred for 15 minutes, allowed to warm to room temperature, stirred for 30 minutes, diluted with EtOAc, washed with water and saturated NH4Cl, dried (Na2SO4), and filtered. The residue was chromatographed on SiO2 (0-10% Et2O/hexanes) to give 561.0 mg of the title compound as a clear gum. 1H NMR (300 MHz, DMSO-d6) δ 7.60 (dd, 1H), 7.46 (dd, 1H), 7.21-7.36 (m, 5H), 7.10 (ddd, 1H), 6.21 (s, 1H), 5.88 (s, 1H).

Workup

  1. stirringstirred for 30 minutes
  2. washwashed with water and saturated NH4Cl
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customThe residue was chromatographed on SiO2 (0-10% Et2O/hexanes)

Sources & evidence

ORD record
ord-097feba1694346f3a3e17d9ca7868bc8
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Linked notes

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