Iodoethane → 1-Bromo-5,6,7,8-tetrahydronaphthalen-2-yl ethyl ether

HRID 1063258Notes

Reaction equation

HRID 1063258 reaction equation
[Br:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][C:3]=1[OH:12].I[CH2:14][CH3:15]>>[CH2:14]([O:12][C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[C:2]=1[Br:1])[CH3:15]

Participants

3

Reactant 2

HCID 6340IodoethaneHCID 222787171-Bromo-5,6,7,8-tetrahydro-2-naphthalenol

Product 1

HCID 222786921-Bromo-5,6,7,8-tetrahydronaphthalen-2-yl ethyl etherYield 66%

Procedure

Following the general procedure of Preparation 1 Step 2 and making non-critical variations but substituting 3-bromo-5,6,7,8-tetrahydronaphthalen-2-ol with 1-bromo-5,6,7,8-tetrahydronaphthalen-2-ol (900 mg, 3.96 mmol) and substituting iodomethane with iodoethane gave 980 mg of a crude oil. The crude was purified by Biotage MPLC (120 g column, 3% ethyl acetate in heptane) to give 657 mg (66%) of 1-bromo-5,6,7,8-tetrahydronaphthalen-2-yl ethyl ether as a white solid.

Workup

  1. customthe general procedure of Preparation 1 Step 2
  2. customgave 980 mg of a crude oil
  3. customThe crude was purified by Biotage MPLC (120 g column, 3% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-ef54049c9af7412c8aa852e73609b54a
Source dataset
uspto-grants-2005_11
Patent number
US06964965B2

Reaction notes

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