N-bromobutanimide → 7-Bromo-6-hydroxy-1-heptanol

HRID 1263272Notes

Reaction equation

HRID 1263272 reaction equation
[CH2:1]([OH:8])[CH2:2][CH2:3][CH2:4]CC=C.[Br:9]N1C(=O)CCC1=O.[C:17]([OH:21])(C)([CH3:19])[CH3:18].O>>[Br:9][CH2:18][CH:17]([OH:21])[CH2:19][CH2:4][CH2:3][CH2:2][CH2:1][OH:8]

Participants

4

Reactant 3

HCID 67184N-bromobutanimide3×HCID 543123Hept-6-en-1-olHCID 714019492-Methylpropan-2-ol--water (1/1)

Product 1

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

Procedure

To a solution of 3 (500 mg, 4.38 mmol) in t-butanol-water (24 mL-4 mL) in the dark was added N-bromosuccinimide (NBS) (858 mg, 4.82 mmol) in small portions. Additional NBS (312 mg) was added after 4 hours and 16 hours later another 400 mg of NBS was added. The reaction mixture was stirred for 68 hours. After removal of t-butanol in vacuo, the residue was diluted with ether, washed with saturated sodium thiosulfite solution, saturated sodium chloride solution, and dried over magnesium sulfate. The crude product was purified by HPLC to give 123 mg of 7-bromo-6-hydroxy-1-heptanol (4).

Workup

  1. additionwas added
  2. customAfter removal of t-butanol in vacuo
  3. additionthe residue was diluted with ether
  4. washwashed with saturated sodium thiosulfite solution, saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customThe crude product was purified by HPLC

Sources & evidence

ORD record
ord-ba6d27e779a340eda1b70c0430433cb5
Source dataset
uspto-grants-1984_06
Patent number
US04456613

Reaction notes

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