Carbon tetrabromide → 3-(5-Fluorobenzothiazol-2-ylmethoxy)benzyl bromide

HRID 1109772Notes

Reaction equation

HRID 1109772 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([CH2:10][O:11][C:12]3[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=3)[CH2:15]O)=[N:7][C:6]=2[CH:20]=1.C(Br)(Br)(Br)[Br:22].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([CH2:10][O:11][C:12]3[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=3)[CH2:15][Br:22])=[N:7][C:6]=2[CH:20]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 536375833-(5-Fluorobenzothiazol-2-ylmethoxy)benzyl alcohol

Product 1

HCID 190194713-(5-Fluorobenzothiazol-2-ylmethoxy)benzyl bromideYield 71.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.04 g of 3-(5-fluorobenzothiazol-2-ylmethoxy)benzyl alcohol (Preparation L) in 60 ml of dry tetrahydrofuran was added 2.38 g of carbontetrabromide and 1.89 g of triphenylphosphine and the reaction stirred under nitrogen at room temperature for 1.5 hours. The reaction mixture was filtered, treated with 100 ml of water and extracted with ethyl acetate. The extracts were washed with water and a brine solution and dried over sodium sulfate. The solvent was removed and the residual brown solid chromatographed on 200 g of silica gel using from 5-10% ethyl acetate--95-90% hexane (v:v). The fractions containing the product were combined and concentrated to give 910 mg of the titled product, m.p. 99°-100° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. additiontreated with 100 ml of water
  3. extractionextracted with ethyl acetate
  4. washThe extracts were washed with water
  5. dry with materiala brine solution and dried over sodium sulfate
  6. customThe solvent was removed
  7. customthe residual brown solid chromatographed on 200 g of silica gel using from 5-10% ethyl acetate--95-90% hexane (v:v)
  8. additionThe fractions containing the product
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-08744490abca494ba1deba0146110a81
Source dataset
uspto-grants-1994_06
Patent number
US05322847

Reaction notes

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