Bromine → HCID 23498867, compound

HRID 1836870Notes

Reaction equation

HRID 1836870 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:14]=[CH:13][C:12]2[C:11]([CH3:16])([CH3:15])[CH2:10][CH2:9][C:8]([CH3:18])([CH3:17])[C:7]=2[CH:6]=1.[Br:19]Br>C(Cl)(Cl)(Cl)Cl.[Fe]>[Br:19][C:14]1[C:5]([CH2:4][CH2:3][CH2:2][OH:1])=[CH:6][C:7]2[C:8]([CH3:18])([CH3:17])[CH2:9][CH2:10][C:11]([CH3:16])([CH3:15])[C:12]=2[CH:13]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 23498951HCID 23498951, compound

Product 1

HCID 23498867HCID 23498867, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 5943Carbon TetrachlorideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 12.3 g (49.8 mmol) of 2-(3-hydroxypropyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene in 100 mL of carbon tetrachloride at 0° C. was added a trace of iron powder followed by a solution of 8.76 g (54.8 mmol) of bromine in 80 mL of carbon tetrachloride. After 4.5 hours at 0° C. the reaction mixture was warmed to room temperature. After 3 hours at room temperature, the reaction mixture was poured into ice water and the mixture was extracted with dichloromethane. The organic fraction was washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (30% ethyl acetate/hexane) to give 10.2 g (63%) of 2-bromo-3-(3-hydroxypropyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene. (M+=324).

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe organic fraction was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography on silica gel (30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4404198138404699a96737c1a6a56604
Source dataset
uspto-grants-2004_08
Patent number
US06777418B2

Reaction notes

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