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

HRID 963706Notes

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-b6211b5f490e4c9ca781cb8cf8edf7e1
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05763489

Reaction notes

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