Hydrogen Bromide → HCID 18536915, compound

HRID 2298612Notes

Reaction equation

HRID 2298612 reaction equation
[O:1]([CH2:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:12][Si](C=[N+]=[N-])(C)C.[BrH:19]>CC#N.CCCCCC.C(O)(=O)C>[Br:19][CH2:12][C:9](=[O:10])[CH2:8][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 260Hydrogen BromideHCID 69703Phenoxyacetyl chlorideHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 18536915HCID 18536915, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolventHCID 8058HexaneSolvent

Procedure

To a solution of 6.c (0.050 mmol) of phenoxyacetyl chloride in 250 μL of anhyd MeCN in a 1-dram short vial (Wheaton Glass) was added 50 μL (0.100 mmol) of a 2 M solution of trimethylsilyldiazomethane in hexane and the vial capped with a PTFE-lined cap. After stirring 1 h at room temperature on a vortex shaker, the mixture was cooled (0° C.) and 21 μL (0.105 mmol) of 30 wt % HBr in acetic acid was added dropwise (gas evolution). After vortexing for 10 min, the mixture was concentrated in vacuo on a vacuum centrifuge concentrator (Speed-Vac, Savant Instruments, Inc.) to provide an amber-colored oil which was used directly in the following step.

Workup

  1. customlined cap
  2. additionwas added dropwise (gas evolution)
  3. waitAfter vortexing for 10 min
  4. concentrationthe mixture was concentrated in vacuo on a vacuum centrifuge concentrator (Speed-Vac, Savant Instruments, Inc.)
  5. customto provide an amber-colored oil which

Sources & evidence

ORD record
ord-f457b65ba538446985da6ed13bdaea72
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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