Water → HCID 57701092, compound

HRID 422878Notes

Reaction equation

HRID 422878 reaction equation
C([Li])(C)(C)C.[CH2:6]([O:13][C:14]1[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[F:21][C:22]1[C:30]([F:31])=[CH:29][CH:28]=[CH:27][C:23]=1[C:24](Cl)=[O:25].O>C1COCC1>[CH2:6]([O:13][C:14]1[CH:19]=[CH:18][C:17]([C:24]([C:23]2[CH:27]=[CH:28][CH:29]=[C:30]([F:31])[C:22]=2[F:21])=[O:25])=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1388351-Bromo-4-phenylmethoxybenzeneHCID 5195492,3-Difluorobenzoyl chlorideHCID 178418306HCID 178418306, compound

Product 1

HCID 57701092HCID 57701092, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-15 °C

Procedure

A solution of t-butyllithium (3.0 mL, 1.2 M in pentane) was added to a cooled (−78° C.) solution of benzyloxy-4-bromobenzene (500 mg, 1.9 mmol) in THF (20 mL). The temperature was raised to −15° C. over a period of 1 h and stirred at −15° C. for an additional 2 h. A slurry of MnCl2.2LiCl2 (1.9 mmol) in THF (13 mL) was added and the mixture was stirred for 30 min allowing the temperature to reach 0° C. 2,3-Difluorobenzoyl chloride was added and the reaction was stirred at r.t. for 1 h. Water (20 mL) was added, stirred for 10 min. The aqueous phase was extracted with dichloromethane (2×20 mL) and the organic phases were combined and washed with brine (20 mL), dried (Na2SO4), filtered and concentrated. Purified by flash chromatography (eluent: 100% heptane →10% ethyl acetate in heptane) to give the title compound 3 (320 mg, 52% yield). 1H-NMR (400 MHz, CDCl3): δ 7.88 (d, J=7.5 Hz, 2H), 7.48-7.15 (m, 8H), 7.08 (d, J=7.5 Hz, 2H), 5.18 (s, 2H).

Workup

  1. stirringthe mixture was stirred for 30 min
  2. customto reach 0° C
  3. stirringthe reaction was stirred at r.t. for 1 h
  4. stirringstirred for 10 min
  5. extractionThe aqueous phase was extracted with dichloromethane (2×20 mL)
  6. washwashed with brine (20 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurified by flash chromatography (eluent: 100% heptane →10% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-d10580e58fe34203913e416d53ad2fdd
Source dataset
uspto-grants-2012_01
Patent number
US08101651B2

Reaction notes

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