Trimethylsilyldiazomethane → 1-(6-Bromonaphthalen-2-yl)-2-diazoethanone

HRID 71830Notes

Reaction equation

HRID 71830 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12](Cl)=[O:13])[CH:6]=[CH:5]2.[Si]([CH:19]=[N+:20]=[N-:21])(C)(C)C>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12](=[O:13])[CH:19]=[N+:20]=[N-:21])[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 218796066-Bromo-2-naphthoyl chloride

Product 1

HCID 768188121-(6-Bromonaphthalen-2-yl)-2-diazoethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

6-Bromonaphthalene-2-carbonyl chloride (27.0 g, crude) was dissolved in dichloromethane (330 mL) and cooled to 0° C. TMS diazomethane solution (100 mL, 2 M in DCM) was added, and ice bath was removed. Reaction mixture was stirred for 16 hours and evaporated under vacuum, giving 1-(6-bromonaphthalen-2-yl)-2-diazoethanone (34.7 g, crude) as an orange solid.

Workup

  1. customice bath was removed
  2. customReaction mixture
  3. customevaporated under vacuum

Sources & evidence

ORD record
ord-2f132ea924ef4c439b2a8c86e4152ca1
Source dataset
uspto-grants-2014_09
Patent number
US08822430B2

Reaction notes

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