Bromine → 4-Bromo-5,6,7,8-tetrahydronaphthalen-1-ol

HRID 1076872Notes

Reaction equation

HRID 1076872 reaction equation
[C:1]1([OH:11])[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[Br:12]Br>C(Cl)(Cl)(Cl)Cl>[Br:12][C:4]1[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[C:1]([OH:11])=[CH:2][CH:3]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 682585,6,7,8-Tetrahydro-1-naphthol

Product 1

HCID 222364764-Bromo-5,6,7,8-tetrahydronaphthalen-1-olYield 22.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

To a solution of 37 grams (0.25 mole) of 5,6,7,8-tetrahydronaphthol in 150 ml of carbon tetrachloride was added dropwise with stirring a solution of 44 grams (0.25 mole) of bromine in 50 ml of carbon tetrachloride. When the addition was complete the mixture was stirred for 30 minutes at room temperature and then evaporated in vacuo to a residue which after two recrystallizations from hexane provided 13 grams (22.9 percent) of product, m.p. 83°-85°C.

Workup

  1. additionWhen the addition
  2. customevaporated in vacuo to a residue which
  3. customafter two recrystallizations from hexane

Sources & evidence

ORD record
ord-09abc6cc51ff4f11b20e62d4f0683c3b
Source dataset
uspto-grants-1976_05
Patent number
US03958006

Reaction notes

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