Hydrochloric Acid → 4-bromo-2-(hydroxymethyl)-6-methoxyphenol

HRID 655650

Reaction equation

HRID 655650 reaction equation
[BH4-].[Na+].C1COCC1.[Br:8][C:9]1[CH:10]=[C:11]([O:18][CH3:19])[C:12]([OH:17])=[C:13]([CH:16]=1)[CH:14]=[O:15].Cl>C(O)(=O)C>[Br:8][C:9]1[CH:10]=[C:11]([O:18][CH3:19])[C:12]([OH:17])=[C:13]([CH2:14][OH:15])[CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 2622385-Bromo-2-hydroxy-3-methoxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 8940924-bromo-2-(hydroxymethyl)-6-methoxyphenolYield 100.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (0.28 g, 6.9 mmol) was added to a THF solution (30 ml) of 5-bromo-2-hydroxy-3-methoxybenzaldehyde (3.2 g 13.8 mmol) under ice cooling and the mixture was stirred at 0° C. for 2 hours. Acetic acid was added to the reaction solution to set pH at 3. 10% hydrochloric acid was added to the reaction mixture, which was then extracted with ethyl acetate. The extracted material was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1→1:1) and concentrated to dryness under reduced pressure to obtain 4-bromo-2-hydroxymethyl-6-methoxyphenol (3.23 g) as light yellow oil.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. dry with materialThe extracted material was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1→1:1)
  5. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-ccc54352225947aa9aa1a81d6c3026d5
Source dataset
uspto-grants-2011_12
Patent number
US08071600B2

Linked notes

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