Potassium Bromide → 7-Bromo-6-hydroxy-1-heptanol

HRID 1263274Notes

Reaction equation

HRID 1263274 reaction equation
[O:1]1[CH2:9][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].[Br-:10].[K+].C(=O)(O)[O-].[Na+]>C(O)(=O)C.O1CCCC1.CCOCC>[Br:10][CH2:9][CH:2]([OH:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8]

Participants

6

Reactant 3

HCID 253877Potassium BromideHCID 516892Sodium BicarbonateHCID 136166735-(Oxiran-2-yl)pentan-1-ol

Product 1

HCID 133660747-Bromo-6-hydroxy-1-heptanol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 23444217Acetic acid tetrahydrofuranSolvent

Procedure

A mixture of 5 (120 mg, 0.9 mmol) in acetic acid-tetrahydrofuran (2 mL-0.4 mL) was treated with 0.3 mL of saturated aqueous potassium bromide solution at room temperature over 67 hours. It was then diluted with ether and poured into saturated aqueous sodium bicarbonate. The separated organic layer was washed with saturated sodium thiosulfite, saturated sodium chloride, and dried over magnesium sulfate. Evaporation of the solvent gave 127 mg of 7-bromo-6-hydroxy-1-heptanol (4).

Workup

  1. washThe separated organic layer was washed with saturated sodium thiosulfite, saturated sodium chloride
  2. dry with materialdried over magnesium sulfate
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-e55ae0ea8bc44e1187f5e1d9052070fc
Source dataset
uspto-grants-1984_06
Patent number
US04456613

Reaction notes

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