4-Bromobenzophenone → HCID 12277679, compound

HRID 449124Notes

Reaction equation

HRID 449124 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:9])=[CH:4][CH:3]=1.[CH3:16][Mg]Br>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)([OH:9])[CH3:16])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70304-BromobenzophenoneHCID 178418573HCID 178418573, compound

Product 1

HCID 12277679HCID 12277679, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of (4-bromophenyl)phenyl methanone (0.750 g, 2.87 mmol) in anhydrous THF (25.00 mL) was added solution of methylmagnesium bromide in THF (3.00 M, 1.91 mL) via a syringe at −78° C. The resulting mixture was stirred for 2 hours at −78° C. The reaction was quenched with 10 mL of a saturated aqueous NH4Cl solution at −78° C. and allowed to warm to rt. The product was extracted with EtOAc (2×) and brine (2×). The aqueous layer was back-extracted with DCM several times. The organic layers were combined, dried, filtered and concentrated in vacuo to give the product which was used for next step without any further purification. 1H NMR (400 MHz, CDCl3): δ 1.90 (3H, s) 7.19-7.33 (5H, m) 7.33-7.43 (4H, m).

Workup

  1. customThe reaction was quenched with 10 mL of a saturated aqueous NH4Cl solution at −78° C.
  2. temperatureto warm to rt
  3. extractionThe product was extracted with EtOAc (2×) and brine (2×)
  4. extractionThe aqueous layer was back-extracted with DCM several times
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give the product which
  9. customwas used for next step without any further purification

Sources & evidence

ORD record
ord-cc9724d5e7d94041b45e08828703da93
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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