Boric Acid → 1-Chloro-3-(4'-fluoro-4-biphenylyl)-butan-3-ol

HRID 1439769Notes

Reaction equation

HRID 1439769 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([N+]([O-])=O)=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)([OH:6])[CH3:5].N([O-])=O.[Na+].B(O)(O)O.[FH:30]>O>[Cl:1][CH2:2][CH2:3][C:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([F:30])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)([OH:6])[CH3:5]

Participants

6

Reactant 4

HCID 7628Boric AcidHCID 14917Hydrofluoric AcidHCID 213964881-Chloro-3-(4'-nitro-4-biphenylyl)-butan-3-olHCID 23668193Sodium Nitrite

Product 1

HCID 203028961-Chloro-3-(4'-fluoro-4-biphenylyl)-butan-3-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3 ml. of concentrated hydrochloric acid are added, at 0°, to 2.78 g. of 1-chloro-3-(4'-amino-4-biphenylyl)-butan-3-ol [which can be obtained by nitrating 1-chloro-3-(4-biphenylyl)-butan- 3-ol and reducing the resulting 1-chloro-3-(4'-nitro-4-biphenylyl)-butan-3-ol] and a solution of 1.4 g. of NaNO2 in 6 ml. of water is then added at 0°, while stirring. After adding a solution of 0.7 g. of boric acid in 1.5 g. of 60% hydrofluoric acid, the mixture is stirred for 40 minutes and filtered and the product is washed with water, methanol and ether and dried and the resulting diazonium fluoborate is heated to about 150° until decomposition is complete to give 1-chloro-3-(4'-fluoro-4-biphenylyl)-butan-3-ol, m.p. 78° - 79°.

Workup

  1. additionAfter adding a solution of 0.7 g
  2. filtrationfiltered
  3. washthe product is washed with water, methanol and ether
  4. customdried
  5. temperaturethe resulting diazonium fluoborate is heated to about 150° until decomposition

Sources & evidence

ORD record
ord-339ba7dc436447d89ca8b8b2ae379615
Source dataset
uspto-grants-1977_11
Patent number
US04060633

Reaction notes

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