Benzoyl chloride, 3-bromo- → HCID 59596284, compound

HRID 2264771Notes

Reaction equation

HRID 2264771 reaction equation
Br[C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C([Mg]Cl)(C)C.[Cl-].[Li+].[Br:18][C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22](Cl)=[O:23].C([Cu])#N>O1CCCC1>[Br:18][C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22]([C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5])=[O:23]

Participants

7

Reactant 5

HCID 74377Benzoyl chloride, 3-bromo-HCID 433294Lithium ChlorideHCID 234985242-Bromo-4-chlorobenzonitrileHCID 178418546HCID 178418546, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 59596284HCID 59596284, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-Bromo-4-chlorobenzonitrile (1.00 g, 4.62 mmol) was added to isopropylmagnesium chloride×lithium chloride complex (1.05 M in tetrahydrofuran, 4.62 mL, 1.05 mmol) at −15° C. under argon atmosphere. After stirring for 1.5 h 3-bromobenzoyl chloride and CuCN×2LiCl complex solution (1M in tetrahydrofuran, 0.092 mL, 0.0924 mmol) were added and the temperature was raised to 0° C. After 2 h stirring the reaction was quenched with saturated aqueous ammonium chloride (10 mL) and diluted with water. The product was extracted with ethyl acetate and the organic phase was washed with water and concentrated. The residue was purified with flash chromatography using dichloromethane in heptane (0% to 100%) affording 1.03 g (70% yield) of the title compound. 1H NMR (DMSO-d6) δ 8.12 (d, J=8.28 Hz, 1 H), 8.00-7.92 (m, 3 H), 7.88 (d, J=2.01 Hz, 1 H), 7.77 (d, J=8.03 Hz, 1 H), 7.60-7.53 (m, 1 H); MS (ES) m/z 320, 322 [M+H]+.

Workup

  1. additionwere added
  2. customwas quenched with saturated aqueous ammonium chloride (10 mL)
  3. additiondiluted with water
  4. extractionThe product was extracted with ethyl acetate
  5. washthe organic phase was washed with water
  6. concentrationconcentrated
  7. customThe residue was purified with flash chromatography

Sources & evidence

ORD record
ord-aed56732773446d19fb37865000a2ea8
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

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