Benzoyl chloride → HCID 19103244, compound

HRID 1198760Notes

Reaction equation

HRID 1198760 reaction equation
[CH3:1][O:2][CH:3]([O:19][CH3:20])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[CH:6][C:5]=1Br.[Li]CCCC.[C:26](Cl)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1COCC1.CCCCCC>[CH3:1][O:2][CH:3]([O:19][CH3:20])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[CH:6][C:5]=1[C:26](=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 18398840HCID 18398840, compoundHCID 178418339Butyllithium

Product 1

HCID 19103244HCID 19103244, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of 2-bromo-5-benzyloxy benzaldehyde dimethyl acetal (Tet. Lett., 22, 5027 (1981)) (52.2 g) in THF (600 mL), cooled to -78° C., was added dropwise a solution of n-BuLi (78 ml, 2.1 M) in hexane. After 15 min. CuBr·SMe2 (32 g) was added in 3 portions. The reaction mixture was stirred at -78° C. until CuBr·SMe2 was dissolved (approx. 1 hr.), then benzoyl chloride (20 mL) was added dropwise. The cooling bath was removed and the reaction mixture was stirred at room temperature over night and was quenched with a saturated NH4Cl solution. The organic phage was diluted with Et2O, washed with H2O (3×), brine, dried (MgSO4) and evaporated to afford the title compound which was used as such for the next step.

Workup

  1. dissolutionwas dissolved (approx. 1 hr.)
  2. customThe cooling bath was removed
  3. customwas quenched with a saturated NH4Cl solution
  4. additionThe organic phage was diluted with Et2O
  5. washwashed with H2O (3×), brine
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-6367bac558d242dba75e8b8e93615910
Source dataset
uspto-grants-1994_01
Patent number
US05281720

Reaction notes

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