Hydrochloric Acid → HCID 67042919, compound

HRID 1429287Notes

Reaction equation

HRID 1429287 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:16]=2[F:22])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[B:28](OC)([O:31]C)[O:29]C.Cl>C1COCC1.CCCCCC.CCOCC>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([B:28]([OH:31])[OH:29])=[C:17]([F:21])[C:16]=2[F:22])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 54184221HCID 54184221, compoundHCID 178418339Butyllithium

Product 1

HCID 67042919HCID 67042919, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
70 °C

Procedure

32.0 g (106 mmol) of 4′-benzyloxy-2,3-difluorobiphenyl (CAS No. 305366-70-5) are dissolved in 250 ml of THF, and 75.0 ml (119 mmol) of a 15% solution of n-butyllithium in hexane are added dropwise at −70° C. When the addition is complete, the mixture is stirred for a further 1 h, and a solution of 13.5 ml (119 mmol) of trimethyl borate in 50 ml of THF is added dropwise. After 1 h, the batch is left to thaw, MTB ether is added, and the mixture is acidified using 2 M hydrochloric acid. The org. phase is separated off, washed with sat. sodium chloride solution and dried over sodium sulfate. The solvent is removed in vacuo, and the residue is heated to 70° C. in 200 ml of heptane/toluene (1:1) with stirring and filtered off with suction after cooling, giving 4′-benzyloxy-2,3-difluorobiphenyl-4-boronic acid as a colourless solid, which is employed in the next step without further purification.

Workup

  1. additionWhen the addition
  2. waitAfter 1 h
  3. additionis added
  4. customphase is separated off
  5. washwashed with sat. sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. customThe solvent is removed in vacuo
  8. stirringwith stirring
  9. filtrationfiltered off with suction
  10. temperatureafter cooling

Sources & evidence

ORD record
ord-d79648bc80e84a9e829a978daef3a9d0
Source dataset
uspto-grants-2015_01
Patent number
US08940184B2

Reaction notes

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