1-Bromo-4-(trimethoxymethyl)benzene → HCID 20075599, compound

HRID 704132Notes

Reaction equation

HRID 704132 reaction equation
[OH:1][CH2:2][C:3]([CH2:8][OH:9])([CH2:6][CH3:7])[CH2:4][SH:5].CO[C:12](OC)(OC)[C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=1>C(N(CC)CC)C>[Br:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]23[S:5][CH2:4][C:3]([CH2:6][CH3:7])([CH2:8][O:9]2)[CH2:2][O:1]3)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 135812791-Bromo-4-(trimethoxymethyl)benzeneHCID 21217019HCID 21217019, compound

Product 1

HCID 20075599HCID 20075599, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

(iv)a) 2,2-Di-(hydroxymethyl)-butanethiol (0.5 g.), trimethyl 4-bromo-orthobenzoate 2 (1.0 g.) and triethylamine (0.1 ml.) were heated at 130°, under a current of nitrogen, for 45 minutes. The volatile components were removed in vacuo (2.00 mm.), at 140°. The residue was purified by chromatography on alumina (alumina Woelm TSC) eluting with 1:6 dichloromethane: hexane, saturated with ammonia. 1-(4-Bromophenyl)-4-ethyl-2,6-dioxa-7-thiabicyclo[2,2,2]octane was obtained as colourless crystals (80 mg.).

Workup

  1. customThe volatile components were removed in vacuo (2.00 mm.), at 140°
  2. customThe residue was purified by chromatography on alumina (alumina Woelm TSC)
  3. washeluting with 1:6 dichloromethane

Sources & evidence

ORD record
ord-c436bd95336e4c189ce3e98cb329d2e6
Source dataset
uspto-grants-1991_01
Patent number
US04985582

Reaction notes

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