Water → 3-Bromobenzophenone

HRID 45451

Reaction equation

HRID 45451 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li]C(C)(C)C.Br[C:14]1[CH:15]=[C:16]([CH:22]=[CH:23][CH:24]=1)[C:17](N(C)C)=[O:18].O>C1COCC1.CCCCC>[Br:1][C:2]1[CH:7]=[C:6]([C:17]([C:16]2[CH:22]=[CH:23][CH:24]=[CH:14][CH:15]=2)=[O:18])[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7961BromobenzeneHCID 33358263-bromo-N,N-dimethylbenzamideHCID 178418306HCID 178418306, compound

Product 1

HCID 705483-BromobenzophenoneYield 93.4%

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-80 °C

Procedure

To a solution of 8.25 g (52.5 mmol) of bromobenzene in 100 mL of THF, 70 mL (105 mmol) of 2.5 M tBuLi in pentane was added dropwise with vigorous stirring for 2 h at −80° C. This mixture was slowly warmed to room temperature and then stirred for 30 min at this temperature. 11.4 g (50 mmol) of 3-bromo-N,N-dimethylbenzamide was added at 0° C., and the resulting mixture was stirred for 12 hr at room temperature. 150 mL of water was added, the organic solvent was evaporated using a rotary evaporator, and the product was extracted with 2×100 mL of dichloromethane. The combined extracts were dried over K2CO3 and then evaporated to dryness. This procedure gave 12.2 g (89%) of 16 which was further used without an additional purification.

Workup

  1. temperatureThis mixture was slowly warmed to room temperature
  2. stirringstirred for 30 min at this temperature
  3. stirringthe resulting mixture was stirred for 12 hr at room temperature
  4. customthe organic solvent was evaporated
  5. customa rotary evaporator
  6. extractionthe product was extracted with 2×100 mL of dichloromethane
  7. dry with materialThe combined extracts were dried over K2CO3
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-bb629087c8004f54a980293da4baaddd
Source dataset
uspto-grants-2013_09
Patent number
US08541522B2

Linked notes

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