1-(4-Bromophenyl)cyclopropane-1-carboxylic acid → (1-(4-Bromophenyl)cyclopropyl)methanol

HRID 1960112Notes

Reaction equation

HRID 1960112 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2([C:17](O)=[O:18])[CH2:16][CH2:15]2)=[CH:10][CH:9]=1>C1COCC1>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2([CH2:17][OH:18])[CH2:15][CH2:16]2)=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 162279661-(4-Bromophenyl)cyclopropane-1-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 20252945(1-(4-Bromophenyl)cyclopropyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiAlH4 (2M in THF) (1.6 mL, 3.20 mmol) was added to a solution of 1-(4-bromophenyl)cyclopropanecarboxylic acid (480 mg, 1.991 mmol) in THF (12 ml) at 0° C. The reaction mixture was stirred at rt for 45 min, then quenched with water (3 mL) at 0° C. The mixture was diluted with EtOAc (30 mL) and 1N aqueous potassium sodium tartrate and stirred at rt for 2 h. The organic layer was removed. Aqueous layer was extracted with EtOAc. Combined organic layers were dried (MgSO4), filtered and concentrated to afford the title compound that was used without further purification. LC-MS calculated for C10H11BrO=226, No ionization. Rt: 2.85/5.5 min.

Workup

  1. customquenched with water (3 mL) at 0° C
  2. additionThe mixture was diluted with EtOAc (30 mL) and 1N aqueous potassium sodium tartrate
  3. stirringstirred at rt for 2 h
  4. customThe organic layer was removed
  5. extractionAqueous layer was extracted with EtOAc
  6. dry with materialCombined organic layers were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-4213aaa63db048b8b76fcb2ab98dec5a
Source dataset
uspto-grants-2013_04
Patent number
US08410284B2

Reaction notes

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