Carbon tetrabromide → 2-(5-Methoxy-1,2,3,4-tetrahydro-1-naphthyl)ethyl bromide

HRID 344039Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][CH:8]2[CH2:13][CH2:14]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:35]C(Br)(Br)Br>ClCCl>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][CH:8]2[CH2:13][CH2:14][Br:35]

Participants

Conditions

Temperature: 5 °C

Procedure

To a solution of 2-(5-methoxy-1,2,3,4-tetrahydro-1-naphthyl)ethanol (0.20 g) and triphenylphosphine (0.42 g) in dichloromethane (10 ml) was added tetrabromomethane (0.90 g) at 5° C. The solution was stirred at 5° C. for 1.5 hours and evaporated in vacuo. To the residue, ethyl acetate was added and the insoluble material was filtered off. The ethyl acetate solution was evaporated in vacuo. The residue was chromatographed (n-hexane) over silica gel to afford 2-(5-methoxy-1,2,3,4-tetrahydro-1-naphthyl)ethyl bromide (0.18 g) as a colorless oil.

Workup

customevaporated in vacuo
additionTo the residue, ethyl acetate was added
filtrationthe insoluble material was filtered off
customThe ethyl acetate solution was evaporated in vacuo
customThe residue was chromatographed (n-hexane) over silica gel

Sources & evidence

ORD record: ord-3251c7b1e6d043a999c253b377ccbdf9
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05863918

Reaction notes

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