Diethyl Ether → 1-(4-Bromophenyl)hexan-1-ol

HRID 15002

Reaction equation

HRID 15002 reaction equation
CC[O:3][CH2:4][CH3:5].[Br:6][C:7]1[CH:14]=[CH:13][C:10](C=O)=[CH:9][CH:8]=1.[CH2:15]1[CH2:19]O[CH2:17][CH2:16]1>>[Br:6][C:7]1[CH:8]=[CH:9][C:10]([CH:4]([OH:3])[CH2:5][CH2:19][CH2:15][CH2:16][CH3:17])=[CH:13][CH:14]=1

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 707414-Bromobenzaldehyde

Product 1

HCID 126030861-(4-Bromophenyl)hexan-1-olYield 76%

Procedure

n-PentylMgBr (29 mL, 58 mmol, 2 M/ether) was added to a 0° C. solution of 4-bromobenzaldehyde (9.953 g, 54 mmol) in THF (100 mL). After 1 h, the reaction was quenched by addition of 200 mL saturated ammonium chloride solution. The resulting mixture was extracted with ethyl acetate (3×100 mL) and the combined ethyl acetate solution was dried (Na2SO4), filtered and evaporated. Purification of the residue by flash chromatography on silica gel gave 4 (10.501 g, 76%).

Workup

  1. customthe reaction was quenched by addition of 200 mL saturated ammonium chloride solution
  2. extractionThe resulting mixture was extracted with ethyl acetate (3×100 mL)
  3. dry with materialthe combined ethyl acetate solution was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customPurification of the residue by flash chromatography on silica gel

Sources & evidence

ORD record
ord-d5f8ba010fcf42e49e299046f5d44489
Source dataset
uspto-grants-2010_06
Patent number
US07732443B2

Linked notes

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