Boron trifluoride etherate → 3-(4-Bromophenyl)propan-1-ol

HRID 217783

Reaction equation

HRID 217783 reaction equation
[BH4-].[Na+].[CH2:3]1[CH2:7][O:6][CH2:5][CH2:4]1.[Br:8][C:9]1[CH:14]=[CH:13]C=[CH:11][C:10]=1CCC(O)=O.B(F)(F)F.CCOCC>CC(OC)(C)C.O>[Br:8][C:9]1[CH:14]=[CH:13][C:5]([CH2:4][CH2:3][CH2:7][OH:6])=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 8000Boron trifluoride etherateHCID 8028Tetrahydrofuran2×HCID 3160103-(2-Bromophenyl)propionic acid2×HCID 4311764Sodium borohydride

Product 1

HCID 105606143-(4-Bromophenyl)propan-1-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
25 °C

Procedure

Sodium borohydride (119.12 g) and THF (5 L) were charged into reactor 1 and temperature adjusted to −20° C. 3-(bromophenyl)propionic acid (1 kg) was charged into reactor 2 with THF (3 L) and stirred at 25° C. until all the solids dissolved. This solution in reactor 2 was transferred to reactor 1 maintaining reactor 1 contents at <0° C. BF3.Et2O (991.4 g) was slowly added into reactor 1 maintaining reactor 1 contents at −20 to −10° C. After addition, the mixture was stirred at −20 to −10° C. for 1 h. The reaction is analysed for completion (3-(bromophenyl)propionic acid <2.5%). Water (2 L) was slowly added into reactor 1 to quench the reaction. (gas evolution). MTBE (5 L) was charged into reactor 1 and phases separation was carried out. The upper layer was collected and lower layer was washed with MTBE (5 L). The upper layer was collected and combined with the layer from the previous step. Adjusted pH value of the organic layer to 8-9 by adding 1N NaOH solution. The organic layer was washed with saturated NaCl solution (2 L) and the upper layer was collected. The organic layer was evaporated down to a colourless oil.

Workup

  1. customadjusted to −20° C
  2. dissolutiondissolved
  3. customThis solution in reactor 2 was transferred to reactor
  4. customat <0° C
  5. additionAfter addition
  6. stirringthe mixture was stirred at −20 to −10° C. for 1 h
  7. customto quench
  8. customthe reaction
  9. custom1 and phases separation
  10. customThe upper layer was collected
  11. washlower layer was washed with MTBE (5 L)
  12. customThe upper layer was collected
  13. additionAdjusted pH value of the organic layer to 8-9 by adding 1N NaOH solution
  14. washThe organic layer was washed with saturated NaCl solution (2 L)
  15. customthe upper layer was collected
  16. customThe organic layer was evaporated down to a colourless oil

Sources & evidence

ORD record
ord-34040895c7734d0f8dcdc8093bf0d886
Source dataset
uspto-grants-2012_06
Patent number
US08198285B2

Linked notes

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