Bromine → HCID 18182603, compound

HRID 1359596Notes

Reaction equation

HRID 1359596 reaction equation
[C:1]([CH2:4][CH:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][CH2:6]1)([OH:3])=[O:2].[Br:14]Br>C(Cl)Cl>[Br:14][C:11]1[CH:12]=[CH:13][C:8]2[O:7][CH2:6][CH:5]([CH2:4][C:1]([OH:3])=[O:2])[C:9]=2[CH:10]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 110194092-(2,3-Dihydro-1-benzofuran-3-yl)acetic acid

Product 1

HCID 18182603HCID 18182603, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-(carboxymethyl)-2,3-dihydro-benzofuran (reference example 16, 1.26 g, 7.7 mmol) in CH2Cl2 (24 mL) is added, dropwise, a solution of Br2 in CH2Cl2 (7 mL, 1 M). On complete addition the solution is stirred for a further 25 min. The reaction mixture is concentrated under vacuum to give the title compound (1.86 g) as a tan solid. 1H NMR (CDCl3) d 2.67 (dd, J=16, 8 Hz, 1H), 2.85 (dd, J=16, 6 Hz, 1H), 3.88 (m, 1H), 4.29 (t, J=8 Hz, 1H), 4.79 (t, J=8 Hz, 1H), 6.69 (d, J=8 Hz, 1H), 7.26 (m, 2H). MS m/z 256/258 Br pattern (M+).

Workup

  1. additionOn complete addition the solution
  2. concentrationThe reaction mixture is concentrated under vacuum

Sources & evidence

ORD record
ord-7526c73386d8453c82d6776db5ef06d2
Source dataset
uspto-grants-2003_07
Patent number
US06599918B2

Reaction notes

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