Acetic Anhydride → 2-[4-(2-Bromoethyl)phenoxy]ethyl acetate

HRID 916794Notes

Reaction equation

HRID 916794 reaction equation
[Br:1][CH2:2][CH2:3][C:4]1[CH:13]=[CH:12][C:7]([O:8][CH2:9][CH2:10][OH:11])=[CH:6][CH:5]=1.[C:14](OC(=O)C)(=[O:16])[CH3:15].C(N(CC)CC)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:14]([O:11][CH2:10][CH2:9][O:8][C:7]1[CH:12]=[CH:13][C:4]([CH2:3][CH2:2][Br:1])=[CH:5][CH:6]=1)(=[O:16])[CH3:15]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 693843602-[4-(2-Bromoethyl)phenoxy]ethanol

Product 1

HCID 693900572-[4-(2-Bromoethyl)phenoxy]ethyl acetate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-[4-(2-bromoethyl)phenoxy]ethanol (900 mg), acetic anhydride (0.5 mL), triethylamine (1.0 mL) and DMAP (13 mg) in DCM (5 mL) was stirred at room temperature for 0.5 h. The reaction was quenched by pouring into aq. NaHCO3 and the organic layer was washed with 2M HCl, dried (MgSO4) and concentrated in vacuo to give the title compound (1.03 g). LCMS RT=3.32 min.

Workup

  1. customThe reaction was quenched
  2. additionby pouring into aq. NaHCO3
  3. washthe organic layer was washed with 2M HCl
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8d581ef81ae6458c93bdd9de33d20e6e
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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