Hydrochloric Acid → HCID 22025300, compound

HRID 489220Notes

Reaction equation

HRID 489220 reaction equation
[BH4-].[Na+].[Br:3][CH2:4][CH2:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=1)=[O:7].Cl>CO>[Br:3][CH2:4][CH2:5][CH:6]([C:8]1[CH:9]=[CH:10][C:11]([Br:14])=[CH:12][CH:13]=1)[OH:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 123821193-Bromo-1-(4-bromophenyl)propan-1-one

Product 1

HCID 22025300HCID 22025300, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaBH4 (1.5 g, 39.7 mmol) was added by portions to a solution of 3-bromo-1-(4-bromophenyl)propan-1-one (11.7 g, 40 mmol) (Preparation 5) in MeOH while keeping the temperature below 10° C. After 1 h at RT, 1N aqueous hydrochloric acid was added at 5° C. to pH=1 and the mixture was concentrated in vacuum. The residue was dissolved in water and extracted three times with DCM. The organic layer was dried over Na2SO4 and concentrated to yield 3-bromo-1-(4-bromophenyl)propan-1-ol as a yellow oil (11.1 g). 1H NMR (CDCl3): 7.47 (2H, d, J=8.3 Hz), 7.22 (2H, d, J=8.3 Hz), 4.87 (1H, br s), 3.50-3.62 (1H, m), 3.31-3.42 (1H, m), 2.35 (1H, OH, br s), 2-2.31 (2H, m).

Workup

  1. customthe temperature below 10° C
  2. concentrationthe mixture was concentrated in vacuum
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted three times with DCM
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-32b59c794ac84cd98faa6e03cfed69c3
Source dataset
uspto-grants-2005_12
Patent number
US06977267B2

Reaction notes

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