Hydrogen Bromide → 10-Bromo-9-oxodecyl acetate

HRID 1194050Notes

Reaction equation

HRID 1194050 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13](Cl)=[O:14])(=[O:3])[CH3:2].[N+](=[CH2:18])=[N-].[BrH:19]>CCOCC>[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13](=[O:14])[CH2:18][Br:19])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 9550DiazomethaneHCID 19995224HCID 19995224, compound

Product 1

HCID 1999523510-Bromo-9-oxodecyl acetate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

9-Acetoxynonanoyl chloride (4.0 g, 17 mmol) was slowly added to a solution of diazomethane (40 mmol) in ether (100 ml) at 0° C. After 1 h at 0° C. concentrated hydrobromic acid (20 ml) was added. After 1 h at 20° C. the ether was separated, dried (MgSO4), and evaporated under reduced pressure to give 10-bromo-9-oxodecyl acetate as a yellow oil (4.4 g 88%); δH (CDCl3) 4.0 (2H, t, O), 3.8 (2H, s, CH2Br), 2.6 (2H, t, CH2CO), 2.0 (3H, s, OAC), 1.1-1.8 (12H, m, (CH2)6).

Workup

  1. customAfter 1 h at 20° C. the ether was separated
  2. dry with materialdried (MgSO4)
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-1eba4eb5107a44dfa4b1c0327b89c032
Source dataset
uspto-grants-1989_03
Patent number
US04812470

Reaction notes

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