Sodium Chloride → 2,6-Difluoro-4-hydroxybenzonitrile

HRID 466492Notes

Reaction equation

HRID 466492 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([O:10]C)[CH:7]=[C:6]([F:12])[C:3]=1[C:4]#[N:5].[Cl-].[Al+3].[Cl-].[Cl-].[Cl-].[Na+]>>[F:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([F:12])[C:3]=1[C:4]#[N:5]

Participants

4

Reactant 3

HCID 5234Sodium ChlorideHCID 27787722,6-Difluoro-4-methoxybenzonitrileHCID 6451240Aluminum(III) Chloride

Product 1

HCID 27787742,6-Difluoro-4-hydroxybenzonitrile

Conditions

Temperature
180 °C

Procedure

A stirred, homogeneous mixture of finely powdered, compound 27 (17.0 g, 0.10 mol), aluminium chloride (29.4 g, 0.22 mol) and sodium chloride (7.1 g, 0.12 mol) was heated to 180° C. over 25 min and then at 180° C. for 1 h (glc and tlc analyses both revealed a complete reaction). Ice-water was added, and the product was extracted into ether (twice). The combined ethereal extracts were washed with water, and the product was extracted into 10% sodium hydroxide (twice) and the combined basic extracts were acidified with 36% hydrochloric acid. The product was extracted into ether (twice), and the combined ethereal extracts were washed with water and dried (MgSO4). The solvent was removed in vacuo to give a fawn solid.

Workup

  1. customa complete reaction)
  2. extractionthe product was extracted into ether (twice)
  3. washThe combined ethereal extracts were washed with water
  4. extractionthe product was extracted into 10% sodium hydroxide (twice) and the combined basic extracts
  5. extractionThe product was extracted into ether (twice), and the combined ethereal extracts
  6. washwere washed with water
  7. dry with materialdried (MgSO4)
  8. customThe solvent was removed in vacuo
  9. customto give a fawn solid

Sources & evidence

ORD record
ord-2f4bdb0a3888460ea89a01d4ed7a2a69
Source dataset
uspto-grants-1992_10
Patent number
US05156763

Reaction notes

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