3-Bromo-4-fluorobenzoyl chloride → HCID 59596269, compound

HRID 2264732Notes

Reaction equation

HRID 2264732 reaction equation
[Br-].[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[Zn+])#[N:3].[Cu](C#N)C#N.[Br-].[Li+].[Br:18][C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][C:27]=1[F:28])[C:22](Cl)=[O:23]>O1CCCC1>[Br:18][C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][C:27]=1[F:28])[C:22]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[C:2]#[N:3])=[O:23]

Participants

6

Reactant 4

HCID 695983-Bromo-4-fluorobenzoyl chlorideHCID 82050Lithium BromideHCID 178418260HCID 178418260, compoundHCID 178509677HCID 178509677, compound

Product 1

HCID 59596269HCID 59596269, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-25 °C

Procedure

To a −20° C. solution of 2-cyanophenylzinc bromide (0.5 M in tetrahydrofuran, 20 mL, 10 mmol) was a solution of copper cyanide (0.94 g, 10.5 mmol) and lithium bromide (1.82 g, 21.0 mmol) in tetrahydrofuran (15 mL) added, the reaction was slowly allowed to reach room temperature, after 15 minutes the reaction mixture was recooled to −25° C. A solution of 3-bromo-4-fluorobenzoyl chloride (1.45 g, 10.5 mmol) in tetrahydrofuran (10 mL) was added, the reaction mixture was stirred at −25° C. 1 h and at room temperature over night. After partition between aqueous ammonium chloride and diethylether, the organic phase was dried over magnesium sulfate and concentrated to give the crude title product which was used without further purification. MS (ESI) m/z 304, 306 [M+1]+.

Workup

  1. customTo a −20° C.
  2. additionadded
  3. customwas recooled to −25° C
  4. wait1 h and at room temperature over night
  5. customAfter partition between aqueous ammonium chloride and diethylether
  6. dry with materialthe organic phase was dried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d661366d80684d54a2a0b18e0f16d2da
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

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