Trimethylsilyldiazomethane → 1-(4-Bromonaphthalen-1-yl)-2-diazoethanone

HRID 79773Notes

Reaction equation

HRID 79773 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12](Cl)=[O:13])=[CH:4][CH:3]=1.[Si]([CH:19]=[N+:20]=[N-:21])(C)(C)C>ClCCl>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12](=[O:13])[CH:19]=[N+:20]=[N-:21])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 147000244-Bromonaphthalene-1-carbonyl chloride

Product 1

HCID 723379011-(4-Bromonaphthalen-1-yl)-2-diazoethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4-Bromo-naphthalene-1-carbonyl chloride (13.8 g) was dissolved in dichloromethane (130 mL) and cooled to 0° C. TMS diazomethane solution (40 mL, 2 M in DCM) was added, and ice bath was removed. Reaction mixture was stirred for 18 hours and evaporated under vacuum, giving 1-(4-bromonaphthalen-1-yl)-2-diazoethanone (13.8 g, crude) as a brown oil.

Workup

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

Sources & evidence

ORD record
ord-e577deac2fa348eeaf348cf0ea32aea5
Source dataset
uspto-grants-2014_09
Patent number
US08841278B2

Reaction notes

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