Hydrogen Bromide → HCID 18470091, compound

HRID 2228896Notes

Reaction equation

HRID 2228896 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]O)[CH:5]=[CH:6][C:7]=1[Cl:8].O.C(OCC)C.[BrH:24]>>[Br:24][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1

Participants

5

Reactant 4

HCID 260Hydrogen BromideHCID 962WaterHCID 3283Diethyl EtherHCID 18470154HCID 18470154, compound

Product 1

HCID 18470091HCID 18470091, compound

Procedure

A solution of 8-(3,4-dichlorophenyl)octan-1-ol (0.66 g) in 48% hydrobromic acid (7 ml) was stirred under reflux for 2 h. Water (20 ml) and diethyl ether (20 ml) were added. The organic layer was separated and the aqueous layer reextracted with diethyl ether (10 ml). The combined organic extracts were washed with water (10 ml), sodium hydrogen carbonate solution (10 ml) and brine (10 ml) and dried over magnesium sulfate. The solution was treated with charcoal, filtered and evaporated under reduced pressure to give 1-bromo-8-(3,4-dichlorophenyl)octane (0.74 g). 1H-NMR (CDCl3) δ 1.2-1.8 (12H, m), 2.55 (2H, t), 3.41 (2H, t), 7.00 (1H, dd), 7.25 (1H, dd) and 7.33 (1H, d).

Workup

  1. temperatureunder reflux for 2 h
  2. customThe organic layer was separated
  3. washThe combined organic extracts were washed with water (10 ml), sodium hydrogen carbonate solution (10 ml) and brine (10 ml)
  4. dry with materialdried over magnesium sulfate
  5. additionThe solution was treated with charcoal
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-718573314d7548a88a6d2a11a38f75ef
Source dataset
uspto-grants-2002_07
Patent number
US06417192B1

Reaction notes

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